Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds

ABSTRACT

The invention relates to benzenesulphonamide derivatives of formula (I), methods and intermediate products for production thereof and use of said compounds, or means comprising said compounds for the control of undesired plants and for the desiccation/defoliation of plants.

CROSS REFERENCE TO RELATED APPLICATION

This application is a 35 USC §371 National Phase Entry Application from PCT/EP2004/003624, filed Apr. 6, 2004, and designating the United States

The present invention relates to benzenesulfonamide derivatives of the formula I

in which the variables are as defined below:

-   -   X¹ is hydrogen or halogen;     -   X² is hydrogen, cyano, CS—NH₂, halogen, C₁-C₆-alkyl or         C₁-C₆-haloalkyl;     -   X³ is hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₃-C₇-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or         phenyl-C₁-C₄-alkyl, where the phenyl radical for its part may be         partially or fully halogenated and/or substituted by one to         three radicals from the group consisting of C₁-C₆-alkyl and         C₁-C₆-alkoxy;     -   Y is a group —C(A)B, SO₂ or SO₂NR²;     -   A is oxygen or sulfur;     -   B is oxygen, sulfur, NR² or a bond;     -   R¹ is hydrogen, halogen, hydroxyl, C₁-C₈-alkyl,         C₃-C₇-cycloalkyl, C₃-C₇-cyclo-alkyl-C₁-C₄-alkyl, C₂-C₈-alkenyl,         C₅-C₇-cycloalkenyl, C₃-C₈-alkynyl, C₁-C₈-alkoxy,         C₃-C₇-cycloalkyloxy, C₂-C₈-alkenyloxy, C₃-C₈-alkynyloxy, aryl,         aryloxy, aryl-C₁-C₄-alkyl;         -   where the 13 last mentioned radicals for their part may be             partially or fully halogenated and/or may be substituted by             one to three substituents from the group consisting of             cyano, NO₂, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,             C₃-C₇-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,             C₃-C₇-cycloalkyloxy, C₂-C₆-alkenyloxy, C₃-C₆-alkynyloxy,             C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, amino,             C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylsulfinyl,             C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,             C₁-C₆-haloalkylsulfonyl, C₁-C₆-alkoxysulfonyl, formyl,             C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,             C₂-C₆-alkenylcarbonyl, C₃-C₆-alkynylcarbonyl, carboxy,             C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,             C₂-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl,             mercaptocarbonyl, C₁-C₆-alkylthiocarbonyl,             C₁-C₆-haloalkylthiocarbonyl, C₂-C₆-alkenylthiocarbonyl,             C₃-C₆-alkynylthiocarbonyl, aminocarbonyl,             C₁-C₆-alkylaminocarbonyl, di(C₁-C₆-alkylamino)carbonyl,             C₁-C₆-haloalkylaminocarbonyl,             di(C₁-C₆-haloalkylamino)carbonyl,             C₂-C₆-alkenyl-aminocarbonyl, di(C₂-C₆-alkenylamino)carbonyl,             C₃-C₆-alkynylamino-carbonyl, di(C₃-C₆-alkynylamino)carbonyl,             phenyl, phenoxy, phenyl-C₁-C₄-alkyl and phenyl-C₁-C₄-alkoxy;         -   four- to six-membered heterocyclyl which may be partially or             fully halogenated and/or substituted by one to three             radicals from the group consisting of C₁-C₆-alkyl and             C₁-C₆-alkoxy; or         -   four- to six-membered heterocyclyl-C₁-C₄-alkyl which may be             partially or fully halogenated and/or substituted by one to             three radicals from the group consisting of C₁-C₆-alkyl and             C₁-C₆-alkoxy; or         -   five- or six-membered heteroaryl having one to four nitrogen             atoms or having one to three nitrogen atoms and one oxygen             or one sulfur atom or having one oxygen or sulfur atom,             which radical may be partially or fully halogenated and/or             substituted by one to three radicals from the group             consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,             C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino and             di(C₁-C₆-alkyl)amino; or         -   five- or six-membered heteroaryl-C₁-C₄-alkyl having one to             four nitrogen atoms or having one to three nitrogen atoms             and one oxygen or one sulfur atom or having one oxygen or             sulfur atom, which radical may be partially or fully             halogenated and/or substituted by one to three radicals from             the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl,             C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino and             di(C₁-C₆-alkyl)amino;     -   R² is hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₃-C₈-alkynyl,         C₃-C₇-cycloalkyl, where the four last mentioned radicals may be         partially or fully halogenated; or     -   R¹ and R² together with the nitrogen atom to which they are         attached form a three- to seven-membered heterocycle which for         its part may be partially or fully halogenated and/or         substituted by one to three radicals from the group consisting         of C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkoxy;     -   Q is a radical from the group consisting of Q¹ to Q³⁹

-   -   A¹ to A¹⁷ are oxygen or sulfur;     -   R³, R⁴, R⁷, R⁸, R¹¹, R¹², R¹⁸, R¹⁹, R²⁷, R²⁹, R³², R³³, R³⁸,         R³⁹, R⁴⁴, R⁴⁵, R⁴⁶ and R⁴⁷ are hydrogen, cyano, hydroxyl,         C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁-C₆-haloalkyl,         C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkenyloxy, C₃-C₆-alkynyl, C₃-C₆-alkynyloxy,         C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, phenyl-C₁-C₆-alkyl,         amino, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino; or     -   R³ and R⁴, R¹¹ and R¹², R¹⁸ and R¹⁹, or R⁴⁶ and R⁴⁷ together         with the atoms to which they are attached form a three- to         seven-membered heterocycle which for its part may be partially         or fully halogenated and/or substituted by one to three radicals         from the group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy;     -   R⁵, R⁶, R⁹, R¹⁰, R¹⁵, R¹⁶, R²⁰, R²¹, R³⁰, R³¹, R³⁵, R³⁶, R⁴¹,         R⁴² and R⁴³ are hydrogen, hydroxyl, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl,         C₂-C₆-haloalkenyl, C₂-C₆-alkenyloxy, C₃-C₆-alkynyl,         C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,         C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxysulfonyl,         C₁-C₆-alkylsulfonyloxy, amino, C₁-C₆-alkylamino or         di(C₁-C₆-alkyl)amino; or     -   R⁵ and R⁶, R⁹ and R¹⁰, R¹⁵ and R¹⁶, R²⁰ and R²¹, or R³⁰ and R³¹         together with the atoms to which they are attached form a three-         to seven-membered heterocycle which for its part may be         partially or fully halogenated and/or substituted by one to         three radicals from the group consisting of C₁-C₆-alkyl and         C₁-C₆-alkoxy;     -   R¹³, R¹⁴, R²², R²³, R²⁵ and R²⁶         -   are hydrogen, halogen or C₁-C₆-alkyl;     -   R¹⁷, R²⁸, R³⁴, R³⁷ and R⁴⁰         -   are hydrogen, halogen, hydroxyl, C₁-C₆-alkyl,             C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy,             C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,             C₁-C₆-haloalkylthio, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,             C₂-C₆-alkenyloxy, C₃-C₆-alkynyl or C₃-C₆-alkynyloxy;     -   R²⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,         C₃-C₆-alkynyl, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino or         di(C₁-C₆-alkyl)amino;         and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates for preparing compounds of formula I, to compositions comprising them and to the use of these derivatives or of the compositions comprising them for controlling unwanted plants.

Furthermore, the invention relates to the use of the compounds of the formula I or of compositions comprising them for the desiccation and/or defoliation of plants.

Further, the invention relates to the preparation of herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I, and to methods for controlling unwanted vegetation or for the desiccation/defoliation of plants using the compounds I.

Substituted phenyluracils are disclosed in the literature, for example in WO 96/07323, WO 96/08151, WO 97/42176 and DE 44 37 197. Phenylpyrazoles are described in WO 95/32188. Bicyclic triazolones are described in WO 02/38562. Furthermore, phenyl-substituted pyrimidin(ethi)ones (WO 96/07647), phenylpyridazones (WO 99/52878) and triazole derivatives (WO 96/18618) are known from the literature. WO 93/03019 discloses phenyl-substituted sulfonamides.

However, the herbicidal or desiccant/defoliant properties of the prior-art compounds and/or their compatibilities with crop plants are not always entirely satisfactory. Accordingly, it was an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

The object also extends to providing novel compounds with desiccant/defoliant action.

We have found that this object is achieved by the benzenesulfonamide derivatives of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling unwanted vegetation using the compounds I.

Furthermore, it has been found that the compounds I are also suitable for desiccating and defoliating plant parts, suitable plants being crop plants, such as cotton, potatoes, oilseed rape, sunflowers, soybeans or broad beans, in particular cotton. In this respect, the invention provides compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for the desiccation and/or defoliation of plants using the compounds I.

Depending on the substitution pattern, the compounds of the formula I may comprise one or more centers of chirality, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. Suitable salts are, in general, the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal action of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-yl-ammonium, di-(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents X², X³, R¹-R⁴⁷ or as radicals on phenyl, heterocyclyl or heteroaryl radicals are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkylene, haloalkyl, cyanoalkyl, phenylalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, alkylenoxy, haloalkoxy, alkylamino, dialkylamino and alkoxyalkyl moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term “halogen” denotes in each case fluorine, chlorine, bromine or iodine.

Examples of Other Meanings are:

-   -   C₁-C₄-alkyl and the alkyl moieties of         C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,         C₂-C₆-alkynyloxycarbonyl-C₁-C₄-alkyl, aryl-C₁-C₄-alkyl,         cycloalkyl-C₁-C₄-alkyl, heterocyclyl-C₁-C₄-alkyl and         heteroaryl-C₁-C₄-alkyl: methyl, ethyl, n-propyl, 1-methylethyl,         n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;     -   C₁-C₆-alkyl and the C₁-C₆-alkyl moieties of C₁-C₆-cyanoalkyl,         C₁-C₆-alkylthio, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino,         C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl,         C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl: C₁-C₄-alkyl as mentioned above,         and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl,         3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,         1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,         2-methylpentyl, 3-methylpentyl, 4-methylpentyl,         1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,         2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,         1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,         1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;     -   C₁-C₈-alkyl: C₁-C₆-alkyl as mentioned above, and also, for         example, heptyl, 2-methylhexyl, 3-methylhexyl,         2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl,         3,3-dimethylpentyl, 2,2-dimethyl-3-methylbutyl, octyl,         2-methylheptyl, 3-methylheptyl, 4-methylheptyl,         2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl,         3,3-dimethylhexyl, 2,2,3-trimethylpentyl, 2,3,3-trimethylpentyl,         2,3,4-trimethylpentyl and 2,2,3,3-tetramethylbutyl;     -   C₃-C₇-cycloalkyl and the C₃-C₇-cycloalkyl moieties of         C₃-C₇-cycloalkyl-C₁-C₄-alkyl and C₃-C₇-cycloalkyloxy: a         monocyclic saturated hydrocarbon having 3 to 7 ring members,         such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and         cycloheptyl;     -   C₅-C₇-cycloalkenyl: a monocyclic unsaturated hydrocarbon having         5 to 7 ring members, for example 1-cyclopentenyl,         2-cyclopentenyl, 3-cyclopentenyl, 2,4-cyclopentadienyl,         1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl,         1,3-cyclohexadienyl, 2,5-cyclohexadienyl, 1-cycloheptenyl,         2-cycloheptenyl, 3-cycloheptenyl, 4-cycloheptenyl,         2,6-cycloheptadienyl, 3,5-cycloheptadienyl;     -   four- to six-membered heterocyclyl: a monocyclic saturated or         partially unsaturated hydrocarbon having four to six ring         members as mentioned above which, in addition to carbon atoms,         may comprise one to four nitrogen atoms, one or two oxygen         atoms, one sulfur atom, one to three nitrogen atoms and one         oxygen or one sulfur atom or one oxygen and one sulfur atom and         which may be attached via a carbon atom or a nitrogen atom,         -   for example 2-oxetanyl, 3-oxetanyl, 3-thiethanyl,             1-azetidinyl, 2-azetidinyl, 1-azetinyl, 2-azetinyl;         -   for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl,             2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,             3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,             5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,             5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl,             5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl,             5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,             5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,             1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,             1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,             1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,             1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl,             1,2,3,4-tetrazolidin-5-yl;         -   for example 1-pyrrolidinyl, 2-isothiazolidinyl,             2-isothiazolidinyl, 1-pyrazolidinyl, 3-oxazolidinyl,             3-thiazolidinyl, 1-imidazolidinyl, 1,2,4-triazolidin-1-yl,             1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,             1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,             1,2,3,4-tetrazolidin-5-yl;         -   for example 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,             2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,             2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,             2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,             4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3-yl,             2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl,             4,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-3-yl,             2,3-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,             2,5-dihydroisoxazol-4-yl, 2,3-dihydroisoxazolyl,             4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-5-yl,             2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl,             2,5-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-3-yl,             4,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-4-yl,             2,3-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl,             2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-5-yl,             2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl,             2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,             3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,             3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl,             4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,             2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-3-yl,             2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl,             4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl,             4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl,             2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl,             2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,             2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-3-yl,             3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,             2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazolyl,             2,3-dihydrothiazol-5-yl, 3,4-dihydrothiazol-3-yl,             3,4-dihydrothiazolyl, 3,4-dihydrothiazol-5-yl,             3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl,             3,4-dihydrothiazolyl;         -   for example 4,5-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl,             4,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-1-yl,             4,5-dihydroisothiazol-1-yl, 2,3-dihydroisothiazol-1-yl,             2,3-dihydropyrazol-1-yl, 4,5-dihydropyrazol-1-yl,             3,4-dihydropyrazol-1-yl, 2,3-dihydroimidazol-1-yl,             4,5-dihydroimidazol-1-yl, 2,5-dihydroimidazol-1-yl,             2,3-dihydrooxazol-2-yl, 3,4-dihydrooxazol-2-yl,             2,3-dihydrothiazol-2-yl, 3,4-dihydrothiazol-2-yl;         -   for example 2-piperidinyl, 3-piperidinyl, 4-piperidinyl,             1,3-dioxan-5-yl, 1,3-dithian-5-yl, 2-tetrahydropyranyl,             4-tetrahydropyranyl, 2-tetrahydrothiopyranyl,             4-tetrahydrothiopyranyl, 3-hexahydropyridazinyl,             4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,             4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl,             2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl,             1,2,4-hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-2-yl,             tetrahydro-1,3-oxazin-6-yl, 2-morpholinyl, 3-morpholinyl;         -   for example 1-piperidinyl, 1-hexahydropyridazinyl,             1-hexahydropyrimidinyl, 1-piperazinyl,             1,3,5-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-1-yl,             tetrahydro-1,3-oxazin-1-yl, 1-morpholinyl;         -   for example 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl,             2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl,             2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl,             2H-thiopyran-6-yl, 5,6-dihydro-4H-1,3-oxazin-2-yl;     -   three- to seven-membered heterocyclyl: four- to six-membered         heterocyclyl as mentioned above, and also         -   for example 2-oxiranyl, 1-aziridinyl, 2-aziridinyl,             2-thiiranyl;         -   for example azepan-2-yl, azepan-3-yl, azepan-4-yl,             oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl,             thiepan-3-yl, thiepan-4-yl, 1,2-diazepan-3-yl,             1,2-diazepan-4-yl, 1,2-diazepan-5-yl;         -   for example azepan-1-yl, 1,2-diazepan-1-yl,             1,4-oxazepan-4-yl, 1,4-thiazepan-4-yl;         -   for example 2,3,6,7-tetrahydro-1H-azepin-2-yl,             2,3,6,7-tetrahydro-1H-azepin-3-yl,             2,3,6,7-tetrahydro-1H-azepin-4-yl,             2,3,4,5-tetrahydro-1H-azepin-2-yl,             2,3,4,5-tetrahydro-1H-azepin-3-yl,             2,3,4,5-tetrahydro-1H-azepin-4-yl, 1H-azepin-2-yl,             1H-azepin-3-yl, 1H-azepin-4-yl, oxepin-2-yl, oxepin-3-yl,             oxepin-4-yl, thiepin-2-yl, thiepin-3-yl, thiepin-4-yl,             1,4-oxazepin-2-yl, 1,4-oxazepin-3-yl, 1,4-oxazepin-5-yl,             1,4-oxazepin-6-yl, 1,4-oxazepin-7-yl, 1,4-thiazepin-2-yl,             1,4-thiazepin-3-yl, 1,4-thiazepin-5-yl, 1,4-thiazepin-6-yl,             1,4-thiazepin-7-yl,             4,5,6,7-tetrahydro-1H-[1,3]-diazepin-2-yl,             4,5,6,7-tetrahydro-1H-[1,3]-diazepin-4-yl,             4,5,6,7-tetrahydro-1H-[1,3]-diazepin-5-yl,             4,5,6,7-tetrahydro-1H-[1,3]-diazepin-6-yl,             4,5,6,7-tetrahydro-1H-[1,3]-diazepin-7-yl,             2,3,4,5-tetrahydro-1H-[1,4]-diazepin-2-yl,             2,3,4,5-tetrahydro-1H-[1,4]-diazepin-3-yl,             2,3,4,5-tetrahydro-1H-[1,4]-diazepin-5-yl,             2,3,4,5-tetrahydro-1H-[1,4]-diazepin-6-yl,             2,3,4,5-tetrahydro-1H-[1,4]-diazepin-7-yl,             2,3-dihydro-1H-[1,2]diazepin-3-yl,             2,3-dihydro-1H-[1,2]diazepin-4-yl,             2,3-dihydro-1H-[1,2]diazepin-5-yl,             2,3-dihydro-1H-[1,2]diazepin-6-yl,             2,3-dihydro-1H-[1,2]diazepin-7-yl,             4,7-dihydro-[1,4]-oxazepin-2-yl,             4,7-dihydro-[1,4]-oxazepin-3-yl,             4,7-dihydro-[1,4]-oxazepin-5-yl,             4,7-dihydro-[1,4]-oxazepin-6-yl,             4,7-dihydro-[1,4]-oxazepin-7-yl,             2,3-dihydro-[1,3]-thiazepin-2-yl,             2,3-dihydro-[1,3]-thiazepin-4-yl,             2,3-dihydro-[1,3]-thiazepin-5-yl,             2,3-dihydro-[1,3]-thiazepin-6-yl,             2,3-dihydro-[1,3]-thiazepin-7-yl;         -   for example azepin-1-yl, 2,3,6,7-tetrahydroazepin-1-yl,             2,3,4,5-tetrahydroazepin-1-yl,             4,5,6,7-tetrahydro-[1,3]-diazepin-1-yl,             2,3,4,5-tetrahydro-[1,4]-diazepin-1-yl,             2,3-dihydro-[1,2]diazepin-1-yl,             4,7-dihydro-[1,4]-oxazepin-4-yl,             2,3-dihydro-[1,3]-thiazepin-3-yl;     -   C₂-C₄-alkenyl and the alkenyl moieties of         C₁-C₆-alkoxycarbonyl-C₂-C₄-alkenyl: ethenyl, 1-propenyl,         2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,         1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,         2-methyl-2-propenyl;     -   C₃-C₆-alkenyl: for example 1-propenyl, 2-propenyl,         1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,         1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,         2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,         4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,         3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,         3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,         3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,         1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,         1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,         3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,         2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,         1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,         4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,         3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,         2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,         1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,         1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,         1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,         1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,         2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,         2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,         3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,         1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,         2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,         1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,         1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;     -   C₂-C₆-alkenyl and the C₂-C₆-alkenyl moieties of         C₂-C₆-alkenyloxy, C₂-C₆-alkenylcarbonyl,         C₂-C₆-alkenyloxycarbonyl, C₂-C₆-alkenyloxycarbonyl-C₁-C₄-alkyl,         C₂-C₆-alkenylthiocarbonyl, C₂-C₆-alkenylaminocarbonyl,         di(C₂-C₆-alkenyl)aminocarbonyl: C₃-C₆-alkenyl as mentioned         above, and also ethenyl;     -   C₂-C₈-alkenyl and the C₂-C₈-alkenyl moieties of         C₂-C₈-alkenyloxy: C₂-C₆-alkenyl as mentioned above, and also,         for example, 1-heptenyl, 2-heptenyl, 3-heptenyl,         2-methyl-1-hexenyl, 2-methyl-2-hexenyl, 2-methyl-3-hexenyl,         2-methyl-4-hexenyl, 2-methyl-5-hexenyl, 3-methyl-1-hexenyl,         3-methyl-2-hexenyl, 3-methyl-3-hexenyl, 3-methyl-4-hexenyl,         3-methyl-5-hexenyl, 2,2-dimethyl-3-pentenyl,         2,2-dimethyl-4-pentenyl, 2,3-dimethyl-1-pentenyl,         2,3-dimethyl-2-pentenyl, 2,3-dimethyl-3-pentenyl,         2,3-dimethyl-4-pentenyl, 2,4-dimethyl-1-pentenyl,         2,4-dimethyl-2-pentenyl, 3,3-dimethyl-1-pentenyl,         2,2-dimethyl-3-methyl-3-butentyl, 1-octenyl, 2-octenyl,         3-octenyl, 4-octenyl, 2-methyl-1-heptenyl, 2-methyl-2-heptenyl,         2-methyl-3-heptenyl, 2-methyl-4-heptenyl, 2-methyl-5-heptenyl,         2-methyl-6-heptenyl, 3-methyl-1-heptenyl, 3-methyl-2-heptenyl,         3-methyl-3-heptenyl, 3-methyl-4-heptenyl, 3-methyl-5-heptenyl,         3-methyl-6-heptenyl, 4-methyl-1-heptenyl, 4-methyl-2-heptenyl,         4-methyl-3-heptenyl, 2,2-dimethyl-3-hexenyl,         2,2-dimethyl-4-hexenyl, 2,2-dimethyl-5-hexenyl,         2,3-dimethyl-1-hexenyl, 2,3-dimethyl-2-hexenyl,         2,3-dimethyl-3-hexenyl, 2,3-dimethyl-4-hexenyl,         2,3-dimethyl-5-hexenyl, 2,4-dimethyl-1-hexenyl,         2,4-dimethyl-2-hexenyl, 2,4-dimethyl-3-hexenyl,         2,4-dimethyl-4-hexenyl, 2,4-dimethyl-5-hexenyl,         3,3-dimethyl-1-hexenyl, 3,3-dimethyl-4-hexenyl,         3,3-dimethyl-5-hexenyl, 2,2,3-trimethyl-3-pentenyl,         2,2,3-trimethyl-4-pentenyl, 2,3,3-trimethyl-1-pentenyl,         2,3,3-trimethyl-4-pentenyl, 2,3,4-trimethyl-1-pentenyl and         2,3,4-trimethyl-2-pentenyl;     -   C₃-C₆-alkynyl and the C₃-C₆-alkynyl moieties of         C₃-C₆-alkynyloxy, C₃-C₆-alkynyl-carbonyl,         C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylthiocarbonyl,         C₃-C₆-alkynyl-aminocarbonyl, di(C₃-C₆-alkynyl)aminocarbonyl: for         example 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,         1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl,         4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,         2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,         1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,         5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,         1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,         3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,         4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,         1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,         2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,         1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and         1-ethyl-1-methyl-2-propynyl;     -   C₃-C₈-alkynyl and the C₃-C₈-alkynyl moieties of         C₃-C₈-alkynyloxy: C₃-C₆-alkynyl as mentioned above, and also,         for example, 1-heptynyl, 2-heptynyl, 3-heptynyl,         2-methyl-3-hexynyl, 2-methyl-4-hexynyl, 2-methyl-5-hexynyl,         3-methyl-1-hexynyl, 3-methyl-4-hexynyl, 3-methyl-5-hexynyl,         2,2-dimethyl-3-pentynyl, 2,2-dimethyl-4-pentynyl,         2,3-dimethyl-4-pentynyl, 3,3-dimethyl-1-pentynyl, 1-octynyl,         2-octynyl, 3-octynyl, 4-octynyl, 2-methyl-3-heptynyl,         2-methyl-4-heptynyl, 2-methyl-5-heptynyl, 2-methyl-6-heptynyl,         3-methyl-1-heptynyl, 3-methyl-4-heptynyl, 3-methyl-5-heptynyl,         3-methyl-6-heptynyl, 4-methyl-1-heptynyl, 4-methyl-2-heptynyl,         2,2-dimethyl-3-hexynyl, 2,2-dimethyl-4-hexynyl,         2,2-dimethyl-5-hexynyl, 2,3-dimethyl-4-hexynyl,         2,3-dimethyl-5-hexynyl, 2,4-dimethyl-5-hexynyl,         3,3-dimethyl-1-hexynyl, 3,3-dimethyl-4-hexynyl,         3,3-dimethyl-5-hexynyl, 2,2,3-trimethyl-3-pentynyl,         2,2,3-trimethyl-4-pentynyl and 2,3,3-trimethyl-4-pentynyl;     -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which         is partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, chloromethyl, dichloromethyl,         trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,         chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,         2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,         2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,         3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,         2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,         2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,         3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,         heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,         1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,         4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;     -   C₁-C₆-haloalkyl and the C₁-C₆-haloalkyl moieties of         C₁-C₆-haloalkylthio, C₁-C₆-haloalkylsulfinyl,         C₁-C₆-haloalkylsulfonyl, C₁-C₆-haloalkylcarbonyl,         C₁-C₆-haloalkylthiocarbonyl, C₁-C₆-haloalkylaminocarbonyl,         di(C₁-C₆-haloalkyl)aminocarbonyl: C₁-C₄-haloalkyl as mentioned         above, and also, for example, 5-fluoropentyl, 5-chloropentyl,         5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl,         6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;     -   C₁-C₈-haloalkyl: C₁-C₆-haloalkyl as mentioned above, and also,         for example, 7-fluoroheptyl, 7-chloroheptyl, 7-bromoheptyl,         7-iodoheptyl, perfluoroheptyl, 8-fluorooctyl, 8-chlorooctyl,         8-bromooctyl, 8-iodooctyl and perfluorooctyl;     -   C₂-C₆-haloalkenyl: a C₂-C₆-alkenyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, for example 2-chlorovinyl, 2-chloroallyl,         3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,         2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromovinyl,         2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,         2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl;     -   C₂-C₈-haloalkenyl: a C₂-C₆-haloalkenyl radical as mentioned         above, and also, for example, 2-chloro-1-heptenyl,         3-chloro-1-heptenyl, 2,3-dichloro-1-heptenyl,         3,3-dichloro-1-heptenyl, 2,3,3-trichloro-1-heptenyl,         2-bromo-1-heptenyl, 3-bromo-1-heptenyl, 2,3-dibromo-1-heptenyl,         3,3-dibromo-1-heptenyl, 2,3,3-tribromo-1-heptenyl,         2-chloro-1-octenyl, 3-chloro-1-octenyl, 2,3-dichloro-1-octenyl,         3,3-dichloro-1-octenyl, 2,3,3-trichloro-1-octenyl,         2-bromo-1-octenyl, 3-bromo-1-octenyl, 2,3-dibromo-1-octenyl,         3,3-dibromo-1-octenyl and 2,3,3-tribromo-1-octenyl;     -   C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, for example 1,1-difluoroprop-2-yn-1-yl,         3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl,         4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,         4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,         5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl and         6-iodohex-5-yn-1-yl;     -   C₁-C₄-alkoxy and the C₁-C₄-alkoxy moieties of         C₁-C₄-alkoxy-C₁-C₄-alkyl and phenyl-C₁-C₄-alkoxy: for example         methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy,         1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;     -   C₁-C₆-alkoxy and the C₁-C₆-alkoxy moieties of         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl,         C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkoxycarbonyl-C₂-C₄-alkenyl, C₁-C₆-alkoxysulfonyl:         C₁-C₄-alkoxy as mentioned above, and also, for example, pentoxy,         1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy,         1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,         1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,         3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,         1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,         2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy,         2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,         1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;     -   C₁-C₈-alkoxy: C₁-C₆-alkoxy as mentioned above, and also, for         example, heptoxy, 2-methylhexoxy, 3-methylhexoxy,         2,2-dimethylpentoxy, 2,3-dimethylpentoxy, 2,4-dimethylpentoxy,         3,3-dimethylpentoxy, 2,2-dimethyl-3-methylbutoxy, octoxy,         2-methylheptoxy, 3-methylheptoxy, 4-methylheptoxy,         2,2-dimethylhexoxy, 2,3-dimethylhexoxy, 2,4-dimethylhexoxy,         3,3-dimethylhexoxy, 2,2,3-trimethylpentoxy,         2,3,3-trimethylpentoxy, 2,3,4-trimethylpentoxy and         2,2,3,3-tetramethylbutoxy;     -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, fluoromethoxy,         difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,         bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,         2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,         2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,         2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,         2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,         3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,         2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,         2,3-difluoropropoxy, 2,3-dichloropropoxy,         3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,         2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,         1-(fluoromethyl)-2-fluoroethoxy,         1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,         4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and         nonafluorobutoxy;     -   C₁-C₆-haloalkoxy and the C₁-C₆-haloalkoxy moieties of         C₁-C₆-haloalkoxycarbonyl: C₁-C₄-haloalkoxy as mentioned above,         and also, for example, 5-fluoropentoxy, 5-chloropentoxy,         5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy,         6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and         dodecafluorohexoxy;     -   C₁-C₆-alkoxy-C₁-C₄-alkyl and the alkyl radicals of         C₁-C₆-alkylthio-C₁-C₄-alkyl: a C₁-C₄-alkyl which is substituted         by C₁-C₆-alkoxy as mentioned above, i.e., for example,         methoxymethyl, ethoxymethyl, propoxymethyl,         (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl,         (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl,         2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl,         2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,         2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,         2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,         2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl,         2-(butoxy)propyl, 2-(1-methylpropoxy)propyl,         2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,         3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl,         3-(1-methylethoxy)propyl, 3-(butoxy)propyl,         3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,         3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,         2-(propoxy)butyl, 2-(1-methylethoxy)-butyl, 2-(butoxy)butyl,         2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,         2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,         3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,         3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,         3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,         4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,         4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and         4-(1,1-dimethylethoxy)butyl;     -   C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is         substituted by C₁-C₆-alkoxycarbonyl as mentioned above, i.e.,         for example, methoxycarbonylmethyl, ethoxycarbonylmethyl,         propoxycarbonylmethyl, (1-methylethoxycarbonyl)methyl,         butoxycarbonylmethyl, (1-methylpropoxycarbonyl)methyl,         (2-methylpropoxycarbonyl)methyl,         (1,1-dimethylethoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl,         2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl,         2-(1-methylethoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl,         2-(1-methylpropoxycarbonyl)ethyl,         2-(2-methylpropoxycarbonyl)ethyl,         2-(1,1-dimethylethoxycarbonyl)ethyl, 2-(methoxycarbonyl)propyl,         2-(ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl,         2-(1-methylethoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl,         2-(1-methylpropoxycarbonyl)propyl,         2-(2-methylpropoxycarbonyl)propyl,         2-(1,1-dimethylethoxycarbonyl)propyl, 3-(methoxycarbonyl)propyl,         3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl,         3-(1-methylethoxycarbonyl)propyl, 3-(butoxycarbonyl)propyl,         3-(1-methylpropoxycarbonyl)propyl,         3-(2-methylpropoxycarbonyl)propyl,         3-(1,1-dimethylethoxycarbonyl)propyl, 2-(methoxycarbonyl)butyl,         2-(ethoxycarbonyl)butyl, 2-(propoxycarbonyl)butyl,         2-(1-methylethoxycarbonyl)butyl, 2-(butoxycarbonyl)butyl,         2-(1-methylpropoxycarbonyl)butyl,         2-(2-methylpropoxycarbonyl)butyl,         2-(1,1-dimethylethoxycarbonyl)butyl, 3-(methoxycarbonyl)butyl,         3-(ethoxycarbonyl)butyl, 3-(propoxycarbonyl)butyl,         3-(1-methylethoxycarbonyl)butyl, 3-(butoxycarbonyl)butyl,         3-(1-methylpropoxycarbonyl)butyl,         3-(2-methylpropoxycarbonyl)butyl,         3-(1,1-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)butyl,         4-(ethoxycarbonyl)butyl, 4-(propoxycarbonyl)butyl,         4-(1-methylethoxycarbonyl)butyl, 4-(butoxycarbonyl)butyl,         4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and         4-(1,1-dimethylethoxycarbonyl)butyl;     -   C₁-C₄-alkylthio: for example methylthio, ethylthio,         n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,         2-methylpropylthio and 1,1-dimethylethylthio;     -   C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above, and also,         for example, pentylthio, methylbutylthio, 2-methylbutylthio,         3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,         hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,         1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,         4-methylpentylthio, 1,1-dimethylbutylthio,         1,2-dimethylbutylthio, 1,3-dimethylbutylthio,         2,2-dimethylbutylthio, 2,3-dimethylbutylthio,         3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,         1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,         1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;     -   C₁-C₈-alkylthio: C₁-C₆-alkylthio as mentioned above and the         alkylthio moieties of C₁-C₈-alkylthio-C₁-C₈-alkyl, and also, for         example, heptylthio, 2-methylhexylthio, 3-methylhexylthio,         2,2-dimethylpentylthio, 2,3-dimethylpentylthio,         2,4-dimethylpentylthio, 3,3-dimethylpentylthio,         2,2-dimethyl-3-methylbutylthio, octylthio, 2-methylheptylthio,         3-methylheptylthio, 4-methylheptylthio, 2,2-dimethylhexylthio,         2,3-dimethylhexylthio, 2,4-dimethylhexylthio,         3,3-dimethylhexylthio, 2,2,3-trimethylpentylthio,         2,3,3-trimethylpentylthio, 2,3,4-trimethylpentylthio and         2,2,3,3-tetramethylbutylthio;     -   C₁-C₆-alkylamino: for example methylamino, ethylamino,         propylamino, 1-methylethylamino, butylamino,         1-methylpropylamino, 2-methylpropylamino,         1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,         2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,         1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,         1,2-dimethylpropylamino, 1-methylpentylamino,         2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,         1,1-dimethylbutylamino, 1,2-dimethylbutylamino,         1,3-dimethylbutylamino, 2,2-dimethylbutylamino,         2,3-dimethylbutylamino, 3,3-dimethylbutylamino,         1-ethylbutylamino, 2-ethylbutylamino,         1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,         1-ethyl-1-methylpropylamino and 1-ethyl-2-methylpropylamino;     -   di(C₁-C₄-alkyl)amino: for example N,N-dimethylamino,         N,N-diethylamino, N,N-dipropylamino, N,N-di(1-methylethyl)amino,         N,N-dibutylamino, N,N-di(1-methylpropyl)amino,         N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino,         N-ethyl-N-methylamino, N-methyl-N-propylamino,         N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino,         N-methyl-N-(1-methylpropyl)-amino,         N-methyl-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,         N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,         N-ethyl-N-(1-methylpropyl)amino,         N-ethyl-N-(2-methylpropyl)amino,         N-ethyl-N-(1,1-dimethylethyl)amino,         N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,         N-(1-methylpropyl)-N-propylamino,         N-(2-methylpropyl)-N-propylamino,         N-(1,1-dimethylethyl)-N-propylamino,         N-butyl-N-(1-methylethyl)amino,         N-(1-methylethyl)-N-(1-methylpropyl)amino,         N-(1-methylethyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,         N-butyl-N-(1-methylpropyl)amino,         N-butyl-N-(2-methylpropyl)amino,         N-butyl-N-(1,1-dimethylethyl)amino,         N-(1-methylpropyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino and         N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;     -   di(C₁-C₆-alkyl)amino and the dialkylamino moieties of         di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl, di(C₁-C₆-alkyl)aminocarbonyl         and di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₆-alkyl:         di(C₁-C₄-alkyl)amino as mentioned above, for example,         N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino,         N-ethyl-N-pentylamino, N-methyl-N-hexylamino and         N-ethyl-N-hexylamino;     -   aryl and the aryl moieties of aryloxy and aryl-C₁-C₄-alkyl: a         monocyclic to tricyclic aromatic carbocycle having 6 to 14 ring         members, such as, for example, phenyl, naphthyl and anthracenyl;     -   5- or 6-membered heteroaryl and the 5- or 6-membered heteroaryl         moieties of 5- or 6-membered heteroaryl-C₁-C₆-alkyl: aromatic 5-         or 6-membered heterocycles which, in addition to carbon atoms,         may comprise one to four nitrogen atoms or one to three nitrogen         atoms and one sulfur or oxygen atom or one oxygen or sulfur atom         as ring members, for example         -   2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl,             3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl,             3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl,             4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl,             5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl,             2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,             1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,             1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl,             1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,             1,3,4-triazol-2-yl and tetrazol-2-yl;         -   2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl,             4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl,             2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl,             1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl and             1,2,4,5-tetrazinyl.

In a particular embodiment, the variables of the compounds of the formula I are as defined below, these definitions being, both on their own and in combination with one another, particular embodiments of the compounds of the formula I:

Preference is given to the benzenesulfonamides of the formula I in which

-   -   X¹ is hydrogen, fluorine or chlorine;         -   particularly preferably hydrogen or fluorine;         -   especially preferably fluorine.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   X² is hydrogen, cyano, CS—NH₂ or halogen;         -   particularly preferably hydrogen, cyano or halogen such as             fluorine and chlorine;         -   especially preferably chlorine.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   X¹ is hydrogen, fluorine or chlorine;         -   particularly preferably hydrogen or fluorine;         -   especially preferably fluorine; and     -   X² is hydrogen, cyano, CS—NH₂ or halogen;         -   particularly preferably hydrogen, cyano, halogen such as             fluorine and chlorine;         -   especially preferably chlorine.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   X³ is hydrogen, cyano, C₁-C₆-alkyl or phenyl-C₁-C₄-alkyl;         -   particularly preferably hydrogen, cyano, C₁-C₄-alkyl, such             as CH₃, and C₂H₅, or benzyl;         -   especially preferably hydrogen or cyano;         -   with extraordinary preference hydrogen.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is a group C(A)B;         -   particularly preferably C(A)B, where A is oxygen;         -   especially preferably C(A)B, where A is oxygen and B is             oxygen or sulfur;         -   with extraordinary preference C(A)B, where A and B are             oxygen.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is a group C(A)B;         -   particularly preferably C(A)B, where A is oxygen;         -   especially preferably C(A)B, where A is oxygen and B is NR².     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is a group C(A)B;         -   particularly preferably C(A)B, where A is oxygen;         -   especially preferably C(A)B, where A is oxygen and B is a             bond.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   R¹ is hydrogen, hydroxyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl,         C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, C₂-C₈-alkenyl,         C₂-C₈-haloalkenyl, C₃-C₈-alkynyl, C₁-C₈-alkoxy,         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkoxycarbonyl-C₂-C₄-alkenyl,         C₂-C₆-alkenyloxycarbonyl-C₁-C₄-alkyl,         C₃-C₆-alkynyloxycarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkylthio-C₁-C₄-alkyl, aryl, aryl-C₁-C₄-alkyl;         -   four- to six-membered heterocyclyl which may be partially or             fully halogenated and/or may carry one to three radicals             from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   four- to six-membered heterocyclyl-C₁-C₄-alkyl which may be             partially or fully halogenated and/or may carry one to three             radicals from the group consisting of C₁-C₄-alkyl and             C₁-C₄-alkoxy;         -   five- or six-membered heteroaryl having one to four nitrogen             atoms or having one to three nitrogen atoms and one oxygen             or one sulfur atom or having one oxygen or sulfur atom,             which radicals may be partially or fully halogenated and/or             may carry one to three radicals from the group consisting of             C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,             C₁-C₄-haloalkoxy, amino, C₁-C₄-alkylamino and             di(C₁-C₄-alkyl)amino;         -   five- or six-membered heteroaryl-C₁-C₄-alkyl having one to             four nitrogen atoms or having one to three nitrogen atoms             and one oxygen or one sulfur atom or having one oxygen or             sulfur atom, which radicals may be partially or fully             halogenated and/or may carry one to three radicals from the             group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;     -   particularly preferably         -   hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,             C₃-C₇-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,             C₃-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,             C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,             C₁-C₄-alkoxycarbonyl-C₂-C₄-alkenyl,             C₂-C₄-alkenyloxycarbonyl-C₁-C₄-alkyl,             C₃-C₆-alkynyloxycarbonyl-C₁-C₄-alkyl,             C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, benzyl;         -   five- or six-membered heterocyclyl which may be partially or             fully halogenated and/or may carry one to three radicals             from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   five- or six-membered heteroaryl having one to four nitrogen             atoms or having one to three nitrogen atoms and one oxygen             or one sulfur atom or having one oxygen or sulfur atom,             which radicals may be partially or fully halogenated and/or             may carry one to three radicals from the group consisting of             C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,             C₁-C₄-haloalkoxy, amino, C₁-C₄-alkylamino and             di(C₁-C₄-alkyl)amino;     -   especially preferably         -   C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₅-C₆-cycloalkyl,             C₂-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,             C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, benzyl;         -   five- or six-membered heterocyclyl which may be partially or             fully halogenated and/or may carry one to three radicals             from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   five- or six-membered heteroaryl having one to four nitrogen             atoms or having one to three nitrogen atoms and one oxygen             or one sulfur atom or having one oxygen or sulfur atom,             where the two last mentioned radicals may be partially or             fully halogenated and/or may carry one to three radicals             from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;     -   with extraordinary preference         -   C₁-C₄-alkyl, such as C₃, C₂H₅, CH(CH₃)₂, —CH₂—CH₂—CH₃,             C₁-C₄-haloalkyl, such as CF₃, C₅-C₆-cycloalkyl,             C₂-C₄-alkenyl, C₃-C₄-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,             C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, benzyl, five- or             six-membered heterocyclyl or five- or six-membered             heteroaryl having one to four nitrogen atoms, where the two             last mentioned radicals may be partially or fully             halogenated and/or may carry one to three radicals from the             group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl,         -   particularly preferably hydrogen, C₁-C₆-alkyl or             C₂-C₆-alkenyl,         -   especially preferably hydrogen or C₁-C₄-alkyl,         -   with extraordinary preference hydrogen, CH₃, C₂H₅ or             CH(CH₃)₂,         -   with most extraordinary preference hydrogen or CH₃.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   R¹ and R² together with the nitrogen atom to which they are         attached form a three- to seven-membered heterocycle which for         its part may be partially or fully halogenated and/or may carry         one to three radicals from the group consisting of C₁-C₆-alkyl,         C₁-C₆-haloalkyl and C₁-C₆-alkoxy;         -   particularly preferably a three- to seven-membered             heterocycle which for its part may be partially or fully             halogenated and/or may carry one to three radicals from the             group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   especially preferably a five- to seven-membered heterocycle             which for its part may be partially or fully halogenated             and/or may carry one to three radicals from the group             consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   with extraordinary preference a five- or six-membered             heterocycle which for its part may be partially or fully             halogenated and/or may carry one to three radicals from the             group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   with most extraordinary preference a heterocycle from the             group consisting of pyrrolidin-1-yl, 2,3-dihydropyrrol-1-yl,             2,5-dihydropyrrol-1-yl, piperidin-1-yl,             1,2,3,4-tetrahydropyridin-1-yl,             1,2,3,6-tetrahydropyridin-1-yl, piperazin-1-yl,             morpholin-4-yl, which heterocycle may for its part be             partially or fully halogenated and/or may carry one to three             radicals from the group consisting of C₁-C₄-alkyl and             C₁-C₄-alkoxy.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is C(A)B, where A and B are oxygen; and     -   R¹ has the preferred meanings mentioned above.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which

-   -   Y is C(A)B, where A is oxygen and B is NR²; and     -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, particularly         preferably hydrogen, C₁-C₆-alkyl or C₂-C₆-alkenyl, especially         preferably hydrogen or C₁-C₄-alkyl, with extraordinary         preference hydrogen, CH₃, C₂H₅ or CH(CH₃)₂; with most         extraordinary preference hydrogen or CH₃;     -   with particular preference     -   Y is C(=A)B, where A is oxygen and B is NR²;     -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl,         -   particularly preferably hydrogen, C₁-C₆-alkyl or             C₂-C₆-alkenyl,         -   especially preferably hydrogen or C₁-C₄-alkyl,         -   with extraordinary preference hydrogen, CH₃, C₂H₅ or             CH(CH₃)₂;         -   with most extraordinary preference hydrogen or CH₃; and     -   R¹ has the preferred meanings mentioned above.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is C(A)B where A is oxygen and B is NR²; and     -   R¹ and R² together with the nitrogen atom to which they are         attached, form a three- to seven-membered heterocycle which for         its part may be partially or fully halogenated and/or may carry         one to three radicals from the group consisting of C₁-C₆-alkyl,         C₁-C₆-haloalkyl and C₁-C₆-alkoxy;         -   particularly preferably a three- to seven-membered             heterocycle which for its part may be partially or fully             halogenated and/or may carry one to three radicals from the             group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   especially preferably a five- to seven-membered heterocycle             which for its part may be partially or fully halogenated             and/or may carry one to three radicals from the group             consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   with extraordinary preference a five- or six-membered             heterocycle which for its part may be partially or fully             halogenated and/or may carry one to three radicals from the             group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;         -   with most extraordinary preference a heterocycle from the             group consisting of pyrrolidin-1-yl, 2,3-dihydropyrrol-1-yl,             2,5-dihydropyrrol-1-yl, piperidin-1-yl,             1,2,3,4-tetrahydropyridin-1-yl,             1,2,3,6-tetrahydropyridin-1-yl, piperazin-1-yl,             morpholin-4-yl, which for its part may be partially or fully             halogenated and/or may carry one to three radicals from the             group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is C(A)B, where A is oxygen and B is a bond; and     -   R¹ has the preferred meanings mentioned above.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is a group SO₂;     -   particularly preferably     -   Y is SO₂; and     -   R¹ has the preferred meanings mentioned above.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Y is a group SO₂NR²;     -   particularly preferably     -   Y is SO₂NR²; and     -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl,         -   particularly preferably hydrogen, C₁-C₆-alkyl or             C₂-C₆-alkenyl,         -   especially preferably hydrogen or C₁-C₄-alkyl,         -   with extraordinary preference hydrogen, CH₃, C₂H₅ or             CH(CH₃)₂;         -   with most extraordinary preference hydrogen or CH₃;     -   especially preferably     -   Y is SO₂NR²;     -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl,         -   particularly preferably hydrogen, C₁-C₆-alkyl or             C₂-C₆-alkenyl,         -   especially preferably hydrogen or C₁-C₄-alkyl,         -   with extraordinary preference hydrogen, CH₃, C₂H₅ or             CH(CH₃)₂;         -   with most extraordinary preference hydrogen or CH₃; and     -   R¹ has the preferred meanings mentioned above.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Q is Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷, Q²⁰, Q²¹, Q²², Q²³,         Q²⁴, Q²⁷, Q³¹, Q³⁴, Q³⁸ or Q³⁹;         -   particularly preferably Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³,             Q¹⁷, Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹;         -   especially preferably Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or             Q³⁹;         -   with extraordinary preference Q²¹, Q³² or Q³⁸.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Q is Q¹, Q², Q³, Q⁴, Q⁶, Q⁷, Q⁸, Q⁹, Q¹⁰, Q¹¹, Q¹², Q¹³, Q¹⁴,         Q¹⁵, Q¹⁶, Q¹⁷, Q¹⁸, Q¹⁹, Q²⁰, Q²¹, Q²², Q²³, Q²⁴, Q²⁵, Q²⁶, Q²⁷,         Q²⁸, Q²⁹, Q³⁰, Q³¹, Q³², Q³³, Q³⁴, Q³⁵, Q³⁶, Q³⁷, Q³⁸ or Q³⁹,         -   particularly preferably Q¹, Q², Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷,             Q²⁰, Q²¹, Q²², Q²³, Q²⁴, Q²⁷, Q³¹, Q³², Q³⁴, Q³⁸ or Q³⁹,         -   especially preferably Q¹, Q², Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷,             Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹,         -   with extraordinary preference Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or             Q³⁹,         -   with most extraordinary preference Q²¹, Q³² or Q³⁸.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which

-   -   Q is Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or Q³⁹;     -   particularly preferably         -   Q⁷, where Y is SO₂, SO₂NR² or C(A)B where B=oxygen or NR²;         -   Q²¹, where Y is SO₂, SO₂NR² or C(A)B where B=oxygen, sulfur             or NR²,         -   preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,         -   more preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,             and X² is hydrogen, cyano or halogen, such as fluorine or             chlorine;         -   Q²²; Q²⁷;         -   Q³², where Y is SO₂, SO₂NR² or C(A)B where B=oxygen, sulfur             or NR²;         -   Q³⁸ or Q³⁹;     -   especially preferably         -   Q²¹, where Y is SO₂, SO₂NR² or C(A)B where B=oxygen, sulfur             or NR²,         -   preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,         -   more preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,             and X² is hydrogen, cyano or halogen, such as fluorine or             chlorine;         -   Q³², where Y is SO₂, SO₂NR² or C(A)B where B=oxygen, sulfur             or NR²; or         -   Q³⁸.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   X¹ is hydrogen, fluorine or chlorine;         -   particularly preferably hydrogen or fluorine;         -   especially preferably fluorine;     -   X² is hydrogen, cyano, CS—NH₂ or halogen;         -   particularly preferably hydrogen, halogen, such as fluorine             or chlorine;         -   especially preferably chlorine; and     -   Q is Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷, Q²⁰, Q²¹, Q²², Q²³,         Q²⁴, Q²⁷, Q³¹, Q³², Q³⁴, Q³⁸ or Q³⁹,         -   particularly preferably Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³,             Q¹⁷, Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹,         -   especially preferably Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or             Q³⁹,         -   with extraordinary preference Q²¹, Q³² or Q³⁸.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Q is Q¹ to Q³⁹; and     -   R³, R⁴, R⁷, R⁸, R¹¹, R¹², R¹⁸, R¹⁹, R²⁷, R²⁹, R³², R³³, R³⁸,         R³⁹, R⁴⁴, R⁴⁵, R⁴⁶ and R⁴⁷ are hydrogen, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,         C₁-C₆-alkylsulfonyl or amino;         -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,             C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or             amino;         -   especially-preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂,             CH₂CF₃, OCH₃, OCHF₂, OCF₂CHF₂, SO₂CH₃ or amino;     -   R⁵, R⁶, R⁹, R¹⁰, R¹⁵, R¹⁶, R²⁰, R²¹, R³⁰, R³¹, R³⁵, R³⁶, R⁴¹,         R⁴² and R⁴³         -   are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,             C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfonyl or amino;         -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,             C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or             amino;         -   especially preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂, OCH₃,             OCHF₂, SO₂CH₃ or amino;     -   R¹³, R¹⁴, R²², R²³, R²⁵ and R²⁶         -   are hydrogen, halogen or C₁-C₄-alkyl;         -   particularly preferably hydrogen, halogen or CH₃;         -   especially preferably hydrogen, chlorine or bromine;     -   R¹⁷, R²⁸, R³⁴, R³⁷ or R⁴⁰         -   are hydrogen, halogen or C₁-C₄-alkyl;         -   particularly preferably hydrogen, halogen or CH₃;         -   especially preferably hydrogen, chlorine or bromine.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Q is Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or Q³⁹,         -   particularly preferably Q²¹, Q³² or Q³⁸;     -   A¹, A⁸, A⁹, A¹⁰, A¹¹, A¹², A¹³, A¹⁵, A¹⁶ and A¹⁷ are oxygen;     -   R⁷, R⁸, R²⁹, R³², R³³, R³⁸, R³⁹, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷         -   are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,             C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfonyl or amino;         -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,             C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or             amino;         -   especially preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂,             CH₂CF₃, OCH₃, OCHF₂, OCF₂CHF₂, SO₂CH₃ or amino;     -   R³⁰, R³¹, R³⁵, R³⁶, R⁴¹, R⁴², R⁴³         -   are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,             C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfonyl or amino;         -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,             C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or             amino;         -   especially preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂, OCH₃,             OCHF₂, SO₂CH₃ or amino; and     -   R³⁴, R³⁷, R⁴⁰         -   are hydrogen, halogen or C₁-C₄-alkyl;         -   particularly preferably hydrogen, halogen or CH₃;         -   especially preferably hydrogen, chlorine or bromine.     -   Preference is also given to the benzenesulfonamide derivatives         of the formula I in which     -   Q is Q¹, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q²¹, Q²³, Q²⁴, Q³¹ or Q³⁴;     -   A¹, A², A³, A⁴, A⁵, A⁶, A⁷, A⁸, A⁹, A¹⁴, A¹⁶ and A¹⁷ are oxygen;         and     -   R³ and R⁴, R⁵ and R⁶, R⁹ and R¹⁰, R¹⁵ and R¹⁶, R¹⁸ and R¹⁹, R²⁰         and R²¹, R³⁰ and R³¹ or R⁴⁶ and R⁴⁷ together with the atoms to         which they are attached form a three- to seven-membered         heterocycle which for its part may be partially or fully         halogenated and/or may carry one to three radicals from the         group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy;     -   particularly preferably     -   Q is Q¹, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q²¹, Q²⁴ or Q³¹;     -   A¹, A², A³, A⁴, A⁶, A⁸, A⁹, A¹⁶ and A¹⁷ are oxygen; and     -   R³ and R⁴, R⁵ and R⁶, R⁹ and R¹⁰, R¹⁵ and R¹⁶, R¹⁸ and R¹⁹, R²⁰         and R²¹, R³⁰ and R³¹ or R⁴⁶ and R⁴⁷ together with the atoms to         which they are attached form a three- to seven-membered         heterocycle which for its part may be partially or fully         halogenated and/or may carry one to three radicals from the         group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy;     -   especially preferably     -   Q is Q⁷ or Q²¹,     -   A⁸, A⁹, A¹⁶ and A¹⁷ are oxygen;     -   R²⁹ is hydrogen, C₁-C₆-alkyl or amino; and     -   R³⁰ and R³¹ or R⁴⁶ and R⁴⁷ together with the atoms to which they         are attached form a three- to seven-membered heterocycle which         for its part may be partially or fully halogenated and/or may         carry one to three radicals from the group consisting of         C₁-C₆-alkyl and C₁-C₆-alkoxy.

Extraordinary preference is given to the compounds of the formula I.1 [corresponds to formula I where X¹=fluorine; X²=chlorine; X³=hydrogen; Y=—C(A)B (where A=oxygen, B=NR²); Q=Q²¹ (where A⁸, A⁹=oxygen, R²⁹=methyl, R³⁰=trifluoromethyl and R³¹=hydrogen)], in particular to the compounds of the formulae I.1.1 to I.1.689 of Table 1, where the definitions of the variables X¹, X², X³, Y, A, B, R¹, R² and Q are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own.

TABLE 1 I.1

No. R¹ R² I.1.1 CH₃ H I.1.2 C₂H₅ H I.1.3 CH₂CH₂CH₃ H I.1.4 CH₂CH₂CH₂CH₃ H I.1.5 CH(CH₃)₂ H I.1.6 CH(CH₃)CH₂CH₃ H I.1.7 CH₂CH(CH₃)₂ H I.1.8 C(CH₃)₃ H I.1.9 CH(CH₃)CH₂CH₂CH₃ H I.1.10 CH₂CH(CH₃)CH₂CH₃ H I.1.11 CH₂CH₂CH(CH₃)₂ H I.1.12 CH₂CHF₂ H I.1.13 CH₂CF₃ H I.1.14 CH₂CH₂Cl H I.1.15 CH₂CH₂Br H I.1.16 CH₂CH₂CN H I.1.17 CH(CH₃)CN H I.1.18 CH₂CH(CH₃)CN H I.1.19 cyclopropyl H I.1.20 CH₂-cyclopropyl H I.1.21 cyclopentyl H I.1.22 CH₂-cyclopentyl H I.1.23 cyclohexyl H I.1.24 CH₂CH═CH₂ H I.1.25 C(CH₃)═CH₂ H I.1.26 CH═CHCH₃ H I.1.27 CH₂CH═CHCH₃ H I.1.28 CH₂CF═CF₂ H I.1.29 CH₂C≡CH H I.1.30 CH(CH₃)—C≡CH H I.1.31 CH₂—CO—OCH₃ H I.1.32 CH₂CH₂—CO—OCH₃ H I.1.33 CH₂—CO—OC₂H₅ H I.1.34 CH(CH₃)—CO—OCH₃ H I.1.35 C(CH₃)₂—CO—OCH₃ H I.1.36 CH═CH—CO—OCH₃ H I.1.37 C(CH₃)₂—CO—OCH₂—CH═CH₂ H I.1.38 CH₂CH₂OCH₃ H I.1.39 CH₂CH₂OC₂H₅ H I.1.40 CH₂CH₂SCH₃ H I.1.41 CH₂CH₂S(O)CH₃ H I.1.42 CH₂CH₂SO₂CH₃ H I.1.43 CH₂(1,3-dioxolanyl) H I.1.44 CH₂(2-furyl) H I.1.45 CH₂(3-furyl) H I.1.46 CH₂(2-thienyl) H I.1.47 CH₂(3-thienyl) H I.1.48 phenyl H I.1.49 2-chlorophenyl H I.1.50 3-chlorophenyl H I.1.51 4-chlorophenyl H I.1.52 2-fluorophenyl H I.1.53 3-fluorophenyl H I.1.54 4-fluorophenyl H I.1.55 2-methylphenyl H I.1.56 3-methylphenyl H I.1.57 4-methylphenyl H I.1.58 2-methoxyphenyl H I.1.59 3-methoxyphenyl H I.1.60 4-methoxyphenyl H I.1.61 2-(methoxycarbonyl)phenyl H I.1.62 3-(methoxycarbonyl)phenyl H I.1.63 4-(methoxycarbonyl)phenyl H I.1.64 2-nitrophenyl H I.1.65 3-nitrophenyl H I.1.66 4-nitrophenyl H I.1.67 2-(dimethylamino)phenyl H I.1.68 3-(dimethylamino)phenyl H I.1.69 4-(dimethylamino)phenyl H I.1.70 2-(trifluoromethyl)phenyl H I.1.71 3-(trifluoromethyl)phenyl H I.1.72 4-(trifluoromethyl)phenyl H I.1.73 3-(phenoxy)phenyl H I.1.74 4-(phenoxy)phenyl H I.1.75 2,4-difluorophenyl H I.1.76 2,4-dichlorophenyl H I.1.77 3,4-difluorophenyl H I.1.78 3,4-dichlorophenyl H I.1.79 3,5-difluorophenyl H I.1.80 3,5-dichlorophenyl H I.1.81 2-pyridyl H I.1.82 3-pyridyl H I.1.83 4-pyridyl H I.1.84 α-naphthyl H I.1.84 benzyl H I.1.86 2-chlorobenzyl H I.1.87 3-chlorobenzyl H I.1.88 4-chlorobenzyl H I.1.89 2-methoxybenzyl H I.1.90 3-methoxybenzyl H I.1.91 4-methoxybenzyl H I.1.92 4-chloro-6-methoxy-1,3-pyrimidin-2-yl H I.1.93 4-methyl-6-rnethoxy-1,3-pyrimidin-2-yl H I.1.94 4-methyl-6-methylamino-1,3-pyrimidin-2-yl H I.1.95 4,6-dimethyl-1,3-pyrimidin-2-yl H I.1.96 4-trifluoromethyl-6-methoxy-1,3-pyrimidin-2-yl H I.1.97 4-methoxy-6-methylamino-1,3-pyrimidin-2-yl H I.1.98 4-difluoromethoxy-6-methyl-1,3-pyrimidin-2-yl H I.1.99 4,6-bis(difluoromethoxy)-1,3-pyrimidin-2-yl H I.1.100 4-methyl-6-methoxy-1,3,5-triazin-2-yl H I.1.101 4,6-dimethyl-1,3,5-triazin-2-yl H I.1.102 4-methylamino-6-methoxy-1,3,5-triazin-2-yl H I.1.103 4-trifluoromethyl-6-methoxy-1,3,5-triazin-2-yl H I.1.104 4,6-dimethoxy-1 3,5-triazin-2-yl H I.1.105 CH₃ CH₃ I.1.106 C₂H₅— CH₃ I.1.107 CH₂CH₂CH₃ CH₃ I.1.108 CH₂CH₂CH₂CH₃ CH₃ I.1.109 CH(CH₃)₂ CH₃ I.1.110 CH(CH₃)C₂H₅ CH₃ I.1.111 CH₂CH(CH₃)₂ CH₃ I.1.112 C(CH₃)₃ CH₃ I.1.113 CH(CH₃)CH₂CH₂CH₃ CH₃ I.1.114 CH₂CH(CH₃)CH₂CH₃ CH₃ I.1.115 CH₂CH₂CH(CH₃)₂ CH₃ I.1.116 CH₂CHF₂ CH₃ I.1.117 CH₂CF₃ CH₃ I.1.118 CH₂CH₂Cl CH₃ I.1.119 CH₂CH₂Br CH₃ I.1.120 CH₂CH₂CN CH₃ I.1.121 CH(CH₃)CN CH₃ I.1.122 CH₂CH(CH₃)CN CH₃ I.1.123 cyclopropyl CH₃ I.1.124 CH₂-cyclopropyl CH₃ I.1.125 cyclopentyl CH₃ I.1.126 CH₂-cyclopentyl CH₃ I.1.127 cyclohexyl CH₃ I.1.128 CH₂CH═CH₂ CH₃ I.1.129 C(CH₃)═CH₂ CH₃ I.1.130 CH═CHCH₃ CH₃ I.1.131 CH₂CH═CHCH₃ CH₃ I.1.132 CH₂CF═CF₂ CH₃ I.1.133 CH₂C═CH CH₃ I.1.134 CH(CH₃)—C═CH CH₃ I.1.135 OH CH₃ I.1.136 OCH₃ CH₃ I.1.137 CH₂—CO—OCH₃ CH₃ I.1.138 CH₂CH₂—CO—OCH₃ CH₃ I.1.139 CH₂—CO—OC₂H₅ CH₃ I.1.140 CH(CH₃)—CO—OCH₃ CH₃ I.1.141 C(CH₃)₂—CO—OCH₃ CH₃ I.1.142 CH═CH—CO—OCH₃ CH₃ I.1.143 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH₃ I.1.144 CH₂CH₂OCH₃ CH₃ I.1.145 CH₂CH₂OC₂H₅ CH₃ I.1.146 CH₂CH₂SCH₃ CH₃ I.1.147 CH₂CH₂S(O)CH₃ CH₃ I.1.148 CH₂CH₂SO₂CH₃ CH₃ I.1.149 CH₂(1,3-dioxolanyl) CH₃ I.1.150 CH₂(2-furyl) CH₃ I.1.151 CH₂(3-furyl) CH₃ I.1.152 CH₂(2-thienyl) CH₃ I.1.153 CH₂(3-thienyl) CH₃ I.1.154 phenyl CH₃ I.1.155 2-chlorophenyl CH₃ I.1.156 3-chlorophenyl CH₃ I.1.157 4-chlorophenyl CH₃ I.1.158 2-fluorophenyl CH₃ I.1.159 3-fluorophenyl CH₃ I.1.160 4-fluorophenyl CH₃ I.1.161 2-methylphenyl CH₃ I.1.162 3-methylphenyl CH₃ I.1.163 4-methylphenyl CH₃ I.1.164 2-methoxyphenyl CH₃ I.1.165 3-methoxyphenyl CH₃ I.1.166 4-methoxyphenyl CH₃ I.1.167 2-(methoxycarbonyl)phenyl CH₃ I.1.168 3-(methoxycarbonyl)phenyl CH₃ I.1.169 4-(methoxycarbonyl)phenyl CH₃ I.1.170 2-nitrophenyl CH₃ I.1.171 3-nitrophenyl CH₃ I.1.172 4-nitrophenyl CH₃ I.1.173 2-(dimethylamino)phenyl CH₃ I.1.174 3-(dimethylamino)phenyl CH₃ I.1.175 4-(dimethylamino)phenyl CH₃ I.1.176 2-(trifluoromethyl)phenyl CH₃ I.1.177 3-(trifluoromethyl)phenyl CH₃ I.1.178 4-(trifluoromethyl)phenyl CH₃ I.1.179 3-(phenoxy)phenyl CH₃ I.1.180 4-(phenoxy)phenyl CH₃ I.1.181 2,4-difluorophenyl CH₃ I.1.182 2,4-dichlorophenyl CH₃ I.1.183 3,4-difluorophenyl CH₃ I.1.184 3,4-dichlorophenyl CH₃ I.1.185 3,5-difluorophenyl CH₃ I.1.186 3,5-dichlorophenyl CH₃ I.1.187 2-pyridyl CH₃ I.1.188 3-pyridyl CH₃ I.1.189 4-pyridyl CH₃ I.1.190 α-naphthyl CH₃ I.1.191 benzyl CH₃ I.1.192 2-chlorobenzyl CH₃ I.1.193 3-chlorobenzyl CH₃ I.1.194 4-chlorobenzyl CH₃ I.1.195 2-methoxybenzyl CH₃ I.1.196 3-methoxybenzyl CH₃ I.1.197 4-methoxybenzyl CH₃ I.1.198 C₂H₅ C₂H₅ I.1.199 CH₂CH₂CH₃ C₂H₅ I.1.200 CH₂CH₂CH₂CH₃ C₂H₅ I.1.201 CH(CH₃)₂ C₂H₅ I.1.202 CH(CH₃)CH₂CH₃ C₂H₅ I.1.203 CH₂CH(CH₃)₂ C₂H₅ I.1.204 C(CH₃)₃ C₂H₅ I.1.205 CH(CH₃)CH₂CH₂CH₃ C₂H₅ I.1.206 CH₂CH(CH₃)CH₂CH₃ C₂H₅ I.1.207 CH₂CH₂CH(CH₃)₂ C₂H₅ I.1.208 CH₂CHF₂ C₂H₅ I.1.209 CH₂CF₃ C₂H₅ I.1.210 CH₂CH₂Cl C₂H₅ I.1.211 CH₂CH₂Br C₂H₅ I.1.212 CH₂CH₂CN C₂H₅ I.1.213 CH(CH₃)CN C₂H₅ I.1.214 CH₂CH(CH₃)CN C₂H₅ I.1.215 cyclopropyl C₂H₅ I.1.216 CH₂-cyclopropyl C₂H₅ I.1.217 cyclopentyl C₂H₅ I.1.218 CH₂-cyclopentyl C₂H₅ I.1.219 cyclohexyl C₂H₅ I.1.220 CH₂CH═CH₂ C₂H₅ I.1.221 C(CH₃)═CH₂ C₂H₅ I.1.222 CH═CHCH₃ C₂H₅ I.1.223 CH₂CH═CHCH₃ C₂H₅ I.1.224 CH₂—CF═CF₂ C₂H₅ I.1.225 CH₂—C≡CH C₂H₅ I.1.226 CH(CH₃)—C≡CH C₂H₅ I.1.227 OH C₂H₅ I.1.228 OCH₃ C₂H₅ I.1.229 CH₂—CO—OCH₃ C₂H₅ I.1.230 CH₂—CH₂—CO—OCH₃ C₂H₅ I.1.231 CH₂—CO—OC₂H₅ C₂H₅ I.1.232 CH(CH₃)—CO—OCH₃ C₂H₅ I.1.233 C(CH₃)₂—CO—OCH₃ C₂H₅ I.1.234 CH═CH—CO—OCH₃ C₂H₅ I.1.235 C(CH₃)₂—CO—OCH₂—CH═CH₂ C₂H₅ I.1.236 CH₂CH₂OCH₃ C₂H₅ I.1.237 CH₂CH₂OC₂H₅ C₂H₅ I.1.238 CH₂CH₂SCH₃ C₂H₅ I.1.239 CH₂CH₂S(O)CH₃ C₂H₅ I.1.240 CH₂CH₂SO₂CH₃ C₂H₅ I.1.241 CH₂(1,3-dioxolanyl) C₂H₅ I.1.242 CH₂(2-furyl) C₂H₅ I.1.243 CH₂(3-furyl) C₂H₅ I.1.244 CH₂(2-thienyl) C₂H₅ I.1.245 CH₂(3-thienyl) C₂H₅ I.1.246 phenyl C₂H₅ I.1.247 2-chlorophenyl C₂H₅ I.1.248 3-chlorophenyl C₂H₅ I.1.249 4-chlorophenyl C₂H₅ I.1.250 2-fluorophenyl C₂H₅ I.1.251 3-fluorophenyl C₂H₅ I.1.252 4-fluorophenyl C₂H₅ I.1.253 2-methylphenyl C₂H₅ I.1.254 3-methylphenyl C₂H₅ I.1.255 4-methylphenyl C₂H₅ I.1.256 2-methoxyphenyl C₂H₅ I.1.257 3-methoxyphenyl C₂H₅ I.1.258 4-methoxyphenyl C₂H₅ I.1.259 2-(methoxycarbonyl)phenyl C₂H₅ I.1.260 3-(methoxycarbonyl)phenyl C₂H₅ I.1.261 4-(methoxycarbonyl)phenyl C₂H₅ I.1.262 2-nitrophenyl C₂H₅ I.1.263 3-nitrophenyl C₂H₅ I.1.264 4-nitrophenyl C₂H₅ I.1.265 2-(dimethylamino)phenyl C₂H₅ I.1.266 3-(dimethylamino)phenyl C₂H₅ I.1.267 4-(dimethylamino)phenyl C₂H₅ I.1.268 2-(trifluoromethyl)phenyl C₂H₅ I.1.269 3-(trifluoromethyl)phenyl C₂H₅ I.1.270 4-(trifluoromethyl)phenyl C₂H₅ I.1.271 3-(phenoxy)phenyl C₂H₅ I.1.272 4-(phenoxy)phenyl C₂H₅ I.1.273 2,4-difluorophenyl C₂H₅ I.1.274 2,4-dichlorophenyl C₂H₅ I.1.275 3,4-difluorophenyl C₂H₅ I.1.276 3,4-dichlorophenyl C₂H₅ I.1.277 3,5-difluorophenyl C₂H₅ I.1.278 3,5-dichlorophenyl C₂H₅ I.1.279 2-pyridyl C₂H₅ I.1.280 3-pyridyl C₂H₅ I.1.281 4-pyridyl C₂H₅ I.1.282 α-naphthyl C₂H₅ I.1.283 benzyl C₂H₅ I.1.284 2-chlorobenzyl C₂H₅ I.1.285 3-chlorobenzyl C₂H₅ I.1.286 4-chlorobenzyl C₂H₅ I.1.287 2-methoxybenzyl C₂H₅ I.1.288 3-methoxybenzyl C₂H₅ I.1.289 4-methoxybenzyl C₂H₅ I.1.290 CH₂CH₂CH₃ CH₂CH₂CH₃ I.1.291 CH₂CH₂CH₂CH₃ CH₂CH₂CH₃ I.1.292 CH(CH₃)₂ CH₂CH₂CH₃ I.1.293 CH(CH₃)CH₂CH₃ CH₂CH₂CH₃ I.1.294 CH₂CH(CH₃)₂ CH₂CH₂CH₃ I.1.295 C(CH₃)₃ CH₂CH₂CH₃ I.1.296 CH(CH₃)CH₂CH₂CH₃ CH₂CH₂CH₃ I.1.297 CH₂CH(CH₃)CH₂CH₃ CH₂CH₂CH₃ I.1.298 CH₂CH₂CH(CH₃)₂ CH₂CH₂CH₃ I.1.299 CH₂CHF₂ CH₂CH₂CH₃ I.1.300 CH₂CF₃ CH₂CH₂CH₃ I.1.301 CH₂CH₂Cl CH₂CH₂CH₃ I.1.302 CH₂CH₂Br CH₂CH₂CH₃ I.1.303 CH₂CH₂CN CH₂CH₂CH₃ I.1.304 CH(CH₃)CN CH₂CH₂CH₃ I.1.305 CH₂CH(CH₃)CN CH₂CH₂CH₃ I.1.306 cyclopropyl CH₂CH₂CH₃ I.1.307 CH₂-cyclopropyl CH₂CH₂CH₃ I.1.308 cyclopentyl CH₂CH₂CH₃ I.1.309 CH₂-cyclopentyl CH₂CH₂CH₃ I.1.310 cyclohexyl CH₂CH₂CH₃ I.1.311 CH₂CH═CH₂ CH₂CH₂CH₃ I.1.312 C(CH₃)═CH₂ CH₂CH₂CH₃ I.1.313 CH═CHCH₃ CH₂CH₂CH₃ I.1.314 CH₂CH═CHCH₃ CH₂CH₂CH₃ I.1.315 CH₂CF═CF₂ CH₂CH₂CH₃ I.1.316 CH₂—C≡CH CH₂CH₂CH₃ I.1.317 CH(CH₃)—C≡CH CH₂CH₂CH₃ I.1.318 OH CH₂CH₂CH₃ I.1.319 OCH₃ CH₂CH₂CH₃ I.1.320 CH₂—CO—OCH₃ CH₂CH₂CH₃ I.1.321 CH₂—CH₂—CO—OCH₃ CH₂CH₂CH₃ I.1.322 CH₂—CO—OC₂H₅ CH₂CH₂CH₃ I.1.323 CH(CH₃)—CO—OCH₃ CH₂CH₂CH₃ I.1.324 C(CH₃)₂—CO—OCH₃ CH₂CH₂CH₃ I.1.325 CH═CH—CO—OCH₃ CH₂CH₂CH₃ I.1.326 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH₂CH₂CH₃ I.1.327 CH₂CH₂OCH₃ CH₂CH₂CH₃ I.1.328 CH₂CH₂OC₂H₅ CH₂CH₂CH₃ I.1.329 CH₂CH₂SCH₃ CH₂CH₂CH₃ I.1.330 CH₂CH₂S(O)CH₃ CH₂CH₂CH₃ I.1.331 CH₂CH₂SO₂CH₃ CH₂CH₂CH₃ I.1.332 CH₂(1,3-dioxolanyl) CH₂CH₂CH₃ I.1.333 CH₂(2-furyl) CH₂CH₂CH₃ I.1.334 CH₂(3-furyl) CH₂CH₂CH₃ I.1.335 CH₂(2-thienyl) CH₂CH₂CH₃ I.1.336 CH₂(3-thienyl) CH₂CH₂CH₃ I.1.337 phenyl CH₂CH₂CH₃ I.1.338 2-chlorophenyl CH₂CH₂CH₃ I.1.339 3-chlorophenyl CH₂CH₂CH₃ I.1.340 4-chlorophenyl CH₂CH₂CH₃ I.1.341 2-fluorophenyl CH₂CH₂CH₃ I.1.342 3-fluorophenyl CH₂CH₂CH₃ I.1.343 4-fluorophenyl CH₂CH₂CH₃ I.1.344 2-methylphenyl CH₂CH₂CH₃ I.1.345 3-methylphenyl CH₂CH₂CH₃ I.1.346 4-methylphenyl CH₂CH₂CH₃ I.1.347 2-methoxyphenyl CH₂CH₂CH₃ I.1.348 3-methoxyphenyl CH₂CH₂CH₃ I.1.349 4-methoxyphenyl CH₂CH₂CH₃ I.1.350 2-(methoxycarbonyl)phenyl CH₂CH₂CH₃ I.1.351 3-(methoxycarbonyl)phenyl CH₂CH₂CH₃ I.1.352 4-(methoxycarbonyl)phenyl CH₂CH₂CH₃ I.1.353 2-nitrophenyl CH₂CH₂CH₃ I.1.354 3-nitrophenyl CH₂CH₂CH₃ I.1.355 4-nitrophenyl CH₂CH₂CH₃ I.1.356 2-(dimethylamino)phenyl CH₂CH₂CH₃ I.1.357 3-(dimethylamino)phenyl CH₂CH₂CH₃ I.1.358 4-(dimethylamino)phenyl CH₂CH₂CH₃ I.1.359 2-(trifluoromethyl)phenyl CH₂CH₂CH₃ I.1.360 3-(trifluoromethyl)phenyl CH₂CH₂CH₃ I.1.361 4-(trifluoromethyl)phenyl CH₂CH₂CH₃ I.1.362 3-(phenoxy)phenyl CH₂CH₂CH₃ I.1.363 4-(phenoxy)phenyl CH₂CH₂CH₃ I.1.364 2,4-difluorophenyl CH₂CH₂CH₃ I.1.365 2,4-dichlorophenyl CH₂CH₂CH₃ I.1.366 3,4-difluorophenyl CH₂CH₂CH₃ I.1.367 3,4-dichlorophenyl CH₂CH₂CH₃ I.1.368 3,5-difluorophenyl CH₂CH₂CH₃ I.1.369 3,5-dichlorophenyl CH₂CH₂CH₃ I.1.370 2-pyridyl CH₂CH₂CH₃ I.1.371 3-pyridyl CH₂CH₂CH₃ I.1.372 4-pyridyl CH₂CH₂CH₃ I.1.373 α-naphthyl CH₂CH₂CH₃ I.1.374 benzyl CH₂CH₂CH₃ I.1.375 2-chlorobenzyl CH₂CH₂CH₃ I.1.376 3-chlorobenzyl CH₂CH₂CH₃ I.1.377 4-chlorobenzyl CH₂CH₂CH₃ I.1.378 2-methoxybenzyl CH₂CH₂CH₃ I.1.379 3-methoxybenzyl CH₂CH₂CH₃ I.1.380 4-methoxybenzyl CH₂CH₂CH₃ I.1.381 CH₂CH₂CH₂CH₃ CH(CH₃)₂ I.1.382 CH(CH₃)₂ CH(CH₃)₂ I.1.383 CH(CH₃)CH₂CH₃ CH(CH₃)₂ I.1.384 CH₂CH(CH₃)₂ CH(CH₃)₂ I.1.385 C(CH₃)₃ CH(CH₃)₂ I.1.386 CH(CH₃)CH₂CH₂CH₃ CH(CH₃)₂ I.1.387 CH₂CH(CH₃)CH₂CH₃ CH(CH₃)₂ I.1.388 CH₂CH₂CH(CH₃)₂ CH(CH₃)₂ I.1.389 CH₂CHF₂ CH(CH₃)₂ I.1.390 CH₂CF₃ CH(CH₃)₂ I.1.391 CH₂CH₂Cl CH(CH₃)₂ I.1.392 CH₂CH₂Br CH(CH₃)₂ I.1.393 CH₂CH₂CN CH(CH₃)₂ I.1.394 CH(CH₃)CN CH(CH₃)₂ I.1.395 CH₂CH(CH₃)CN CH(CH₃)₂ I.1.396 cyclopropyl CH(CH₃)₂ I.1.397 CH₂-cyclopropyl CH(CH₃)₂ I.1.398 cyclopentyl CH(CH₃)₂ I.1.399 CH₂-cyclopentyl CH(CH₃)₂ I.1.400 cyclohexyl CH(CH₃)₂ I.1.401 CH₂CH═CH₂ CH(CH₃)₂ I.1.402 C(CH₃)═CH₂ CH(CH₃)₂ I.1.403 CH═CHCH₃ CH(CH₃)₂ I.1.404 CH₂CH═CHCH₃ CH(CH₃)₂ I.1.405 CH₂CF═CF₂ CH (CH₃)₂ I.1.406 CH₂—C≡CH CH(CH₃)₂ I.1.407 CH(CH₃)—C≡CH CH(CH₃)₂ I.1.408 OH CH(CH₃)₂ I.1.409 OCH₃ CH(CH₃)₂ I.1.410 CH₂—CO—OCH₃ CH(CH₃)₂ I.1.411 CH₂—CH₂—CO—OCH₃ CH(CH₃)₂ I.1.412 CH₂—CO—OC₂H₅ CH(CH₃)₂ I.1.413 CH(CH₃)—CO—OCH₃ CH(CH₃)₂ I.1.414 C(CH₃)₂—CO—OCH₃ CH(CH₃)₂ I.1.415 CH═CH—CO—OCH₃ CH(CH₃)₂ I.1.416 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH(CH₃)₂ I.1.417 CH₂CH₂OCH₃ CH(CH₃)₂ I.1.418 CH₂CH₂OC₂H₅ CH(CH₃)₂ I.1.419 CH₂CH₂SCH₃ CH(CH₃)₂ I.1.420 CH₂CH₂S(O)CH₃ CH(CH₃)₂ I.1.421 CH₂CH₂SO₂CH₃ CH(CH₃)₂ I.1.422 CH₂(1,3-dioxolanyl) CH(CH₃)₂ I.1.423 CH₂(2-furyl) CH(CH₃)₂ I.1.424 CH₂(3-furyl) CH(CH₃)₂ I.1.425 CH₂(2-thienyl) CH(CH₃)₂ I.1.426 CH₂(3-thienyl) CH(CH₃)₂ I.1.427 phenyl CH(CH₃)₂ I.1.428 2-chlorophenyl CH(CH₃)₂ I.1.429 3-chlorophenyl CH(CH₃)₂ I.1.430 4-chlorophenyl CH(CH₃)₂ I.1.431 2-fluorophenyl CH(CH₃)₂ I.1.432 3-fluorophenyl CH(CH₃)₂ I.1.433 4-fluorophenyl CH(CH₃)₂ I.1.434 2-methylphenyl CH(CH₃)₂ I.1.435 3-methylphenyl CH(CH₃)₂ I.1.436 4-methylphenyl CH(CH₃)₂ I.1.437 2-methoxyphenyl CH(CH₃)₂ I.1.438 3-methoxyphenyl CH(CH₃)₂ I.1.439 4-methoxyphenyl CH(CH₃)₂ I.1.440 2-(methoxycarbonyl)phenyl CH(CH₃)₂ I.1.441 3-(methoxycarbonyl)phenyl CH(CH₃)₂ I.1.442 4-(methoxycarbonyl)phenyl CH(CH₃)₂ I.1.443 2-nitrophenyl CH(CH₃)₂ I.1.444 3-nitrophenyl CH(CH₃)₂ I.1.445 4-nitrophenyl CH(CH₃)₂ I.1.446 2-(dimethylamino)phenyl CH(CH₃)₂ I.1.447 3-(dimethylamino)phenyl CH(CH₃)₂ I.1.448 4-(dimethylamino)phenyl CH(CH₃)₂ I.1.449 2-(trifluoromethyl)phenyl CH(CH₃)₂ I.1.450 3-(trifluoromethyl)phenyl CH(CH₃)₂ I.1.451 4-(trifluoromethyl)phenyl CH(CH₃)₂ I.1.452 3-(phenoxy)phenyl CH(CH₃)₂ I.1.453 4-(phenoxy)phenyl CH(CH₃)₂ I.1.454 2,4-difluorophenyl CH(CH₃)₂ I.1.455 2,4-dichlorophenyl CH(CH₃)₂ I.1.456 3,4-difluorophenyl CH(CH₃)₂ I.1.457 3,4-dichlorophenyl CH(CH₃)₂ I.1.458 3,5-difluorophenyl CH(CH₃)₂ I.1.459 3,5-dichlorophenyl CH(CH₃)₂ I.1.460 2-pyridyl CH(CH₃)₂ I.1.461 3-pyridyl CH(CH₃)₂ I.1.462 4-pyridyl CH(CH₃)₂ I.1.463 α-naphthyl CH(CH₃)₂ I.1.464 benzyl CH(CH₃)₂ I.1.465 2-chlorobenzyl CH(CH₃)₂ I.1.466 3-chlorobenzyl CH(CH₃)₂ I.1.467 4-chlorobenzyl CH(CH₃)₂ I.1.468 2-methoxybenzyl CH(CH₃)₂ I.1.469 3-methoxybenzyl CH(CH₃)₂ I.1.470 4-methoxybenzyl CH(CH₃)₂ I.1.471 CH(CH₃)CH₂CH₃ CH₂CH₂CH₂CH₃ I.1.472 CH₂CH(CH₃)₂ CH₂CH₂CH₂CH₃ I.1.473 C(CH₃)₃ CH₂CH₂CH₂CH₃ I.1.474 CH(CH₃)CH₂CH₂CH₃ CH₂CH₂CH₂CH₃ I.1.475 CH₂CH(CH₃)CH₂CH₃ CH₂CH₂CH₂CH₃ I.1.476 CH₂CH₂CH(CH₃)₂ CH₂CH₂CH₂CH₃ I.1.477 CH₂CHF₂ CH₂CH₂CH₂CH₃ I.1.478 CH₂CF₃ CH₂CH₂CH₂CH₃ I.1.479 CH₂CH₂Cl CH₂CH₂CH₂CH₃ I.1.480 CH₂CH₂Br CH₂CH₂CH₂CH₃ I.1.481 CH₂CH₂CN CH₂CH₂CH₂CH₃ I.1.482 CH(CH₃)CN CH₂CH₂CH₂CH₃ I.1.483 CH₂CH(CH₃)CN CH₂CH₂CH₂CH₃ I.1.484 cyclopropyl CH₂CH₂CH₂CH₃ I.1.485 CH₂-cyclopropyl CH₂CH₂CH₂CH₃ I.1.486 cyclopentyl CH₂CH₂CH₂CH₃ I.1.487 CH₂-cyclopentyl CH₂CH₂CH₂CH₃ I.1.488 cyclohexyl CH₂CH₂CH₂CH₃ I.1.489 CH₂CH═CH₂ CH₂CH₂CH₂CH₃ I.1.490 C(CH₃)═CH₂ CH₂CH₂CH₂CH₃ I.1.491 CH═CHCH₃ CH₂CH₂CH₂CH₃ I.1.492 CH₂CH═CHCH₃ CH₂CH₂CH₂CH₃ I.1.493 CH₂CF═CF₂ CH₂CH₂CH₂CH₃ I.1.494 CH₂—C≡CH CH₂CH₂CH₂CH₃ I.1.495 CH(CH₃)—C≡CH CH₂CH₂CH₂CH₃ I.1.496 OH CH₂CH₂CH₂CH₃ I.1.497 OCH₃ CH₂CH₂CH₂CH₃ I.1.498 CH₂—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.499 CH₂—CH₂—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.500 CH₂—CO—OC₂H₅ CH₂CH₂CH₂CH₃ I.1.501 CH(CH₃)—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.502 C(CH₃)₂—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.503 CH═CH—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.504 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH₂CH₂CH₂CH₃ I.1.505 CH₂CH₂OCH₃ CH₂CH₂CH₂CH₃ I.1.506 CH₂CH₂OC₂H₅ CH₂CH₂CH₂CH₃ I.1.507 CH₂CH₂SCH₃ CH₂CH₂CH₂CH₃ I.1.508 CH₂CH₂S(O)CH₃ CH₂CH₂CH₂CH₃ I.1.509 CH₂CH₂SO₂CH₃ CH₂CH₂CH₂CH₃ I.1.510 CH₂(1,3-dioxolanyl) CH₂CH₂CH₂CH₃ I.1.511 CH₂(2-furyl) CH₂CH₂CH₂CH₃ I.1.512 CH₂(3-furyl) CH₂CH₂CH₂CH₃ I.1.513 CH₂(2-thienyl) CH₂CH₂CH₂CH₃ I.1.514 CH₂(3-thienyl) CH₂CH₂CH₂CH₃ I.1.515 phenyl CH₂CH₂CH₂CH₃ I.1.516 2-chlorophenyl CH₂CH₂CH₂CH₃ I.1.517 3-chlorophenyl CH₂CH₂CH₂CH₃ I.1.518 4-chlorophenyl CH₂CH₂CH₂CH₃ I.1.519 2-fluorophenyl CH₂CH₂CH₂CH₃ I.1.520 3-fluorophenyl CH₂CH₂CH₂CH₃ I.1.521 4-fluorophenyl CH₂CH₂CH₂CH₃ I.1.522 2-methylphenyl CH₂CH₂CH₂CH₃ I.1.523 3-methylphenyl CH₂CH₂CH₂CH₃ I.1.524 4-methylphenyl CH₂CH₂CH₂CH₃ I.1.525 2-methoxyphenyl CH₂CH₂CH₂CH₃ I.1.526 3-methoxyphenyl CH₂CH₂CH₂CH₃ I.1.527 4-methoxyphenyl CH₂CH₂CH₂CH₃ I.1.528 2-(methoxycarbonyl)phenyl CH₂CH₂CH₂CH₃ I.1.529 3-(methoxycarbonyl)phenyl CH₂CH₂CH₂CH₃ I.1.530 4-(methoxycarbonyl)phenyl CH₂CH₂CH₂CH₃ I.1.531 2-nitrophenyl CH₂CH₂CH₂CH₃ I.1.532 3-nitrophenyl CH₂CH₂CH₂CH₃ I.1.689 4-nitrophenyl CH₂CH₂CH₂CH₃ I.1.534 2-(dimethylamino)phenyl CH₂CH₂CH₂CH₃ I.1.535 3-(dimethylamino)phenyl CH₂CH₂CH₂CH₃ I.1.536 4-(dimethylamino)phenyl CH₂CH₂CH₂CH₃ I.1.537 2-(trifluoromethyl)phenyl CH₂CH₂CH₂CH₃ I.1.538 3-(trifluoromethyl)phenyl CH₂CH₂CH₂CH₃ I.1.539 4-(trifluoromethyl)phenyl CH₂CH₂CH₂CH₃ I.1.540 3-(phenoxy)phenyl CH₂CH₂CH₂CH₃ I.1.541 4-(phenoxy)phenyl CH₂CH₂CH₂CH₃ I.1.542 2,4-difluorophenyl CH₂CH₂CH₂CH₃ I.1.543 2,4-dichlorophenyl CH₂CH₂CH₂CH₃ I.1.544 3,4-difluorophenyl CH₂CH₂CH₂CH₃ I.1.545 3,4-dichlorophenyl CH₂CH₂CH₂CH₃ I.1.546 3,5-difluorophenyl CH₂CH₂CH₂CH₃ I.1.547 3,5-dichlorophenyl CH₂CH₂CH₂CH₃ I.1.548 2-pyridyl CH₂CH₂CH₂CH₃ I.1.549 3-pyridyl CH₂CH₂CH₂CH₃ I.1.550 4-pyridyl CH₂CH₂CH₂CH₃ I.1.551 α-naphthyl CH₂CH₂CH₂CH₃ I.1.552 benzyl CH₂CH₂CH₂CH₃ I.1.553 2-chlorobenzyl CH₂CH₂CH₂CH₃ I.1.554 3-chlorobenzyl CH₂CH₂CH₂CH₃ I.1.555 4-chlorobenzyl CH₂CH₂CH₂CH₃ I.1.556 2-methoxybenzyl CH₂CH₂CH₂CH₃ I.1.557 3-methoxybenzyl CH₂CH₂CH₂CH₃ I.1.558 4-methoxybenzyl CH₂CH₂CH₂CH₃ I.1.559 CH(CH₃)CH₂CH₃ CH₂CH(CH₃)₂ I.1.560 CH₂CH(CH₃)₂ CH₂CH(CH₃)₂ I.1.561 CH(CH₃)CH₂CH₂CH₃ CH₂CH(CH₃)₂ I.1.562 CH₂CH(CH₃)CH₂CH₃ CH₂CH(CH₃)₂ I.1.563 CH₂CH₂CH(CH₃)₂ CH₂CH(CH₃)₂ I.1.564 CH₂CHF₂ CH₂CH(CH₃)₂ I.1.565 CH₂CF₃ CH₂CH(CH₃)₂ I.1.566 CH₂CH₂Cl CH₂CH(CH₃)₂ I.1.567 CH₂CH₂Br CH₂CH(CH₃)₂ I.1.568 CH₂CH₂CN CH₂CH(CH₃)₂ I.1.569 CH(CH₃)CN CH₂CH(CH₃)₂ I.1.570 CH₂CH(CH₃)CN CH₂CH(CH₃)₂ I.1.571 cyclopropyl CH₂CH(CH₃)₂ I.1.572 CH₂-cyclopropyl CH₂CH(CH₃)₂ I.1.573 cyclopentyl CH₂CH(CH₃)₂ I.1.574 CH₂-cyclopentyl CH₂CH(CH₃)₂ I.1.575 cyclohexyl CH₂CH(CH₃)₂ I.1.576 CH₂CH═CH₂ CH₂CH(CH₃)₂ I.1.577 C(CH₃)═CH₂ CH₂CH(CH₃)₂ I.1.578 CH═CHCH₃ CH₂CH(CH₃)₂ I.1.579 CH₂CH═CHCH₃ CH₂CH(CH₃)₂ I.1.580 CH₂CF═CF₂ CH₂CH(CH₃)₂ I.1.581 CH₂—C≡CH CH₂CH(CH₃)₂ I.1.582 CH(CH₃)—C≡CH CH₂CH(CH₃)₂ I.1.583 OH CH₂CH(CH₃)₂ I.1.584 OCH₃ CH₂CH(CH₃)₂ I.1.585 CH₂—CO—OCH₃ CH₂CH(CH₃)₂ I.1.586 CH₂—CH₂—CO—OCH₃ CH₂CH(CH₃)₂ I.1.587 CH₂—CO—OC₂H₅ CH₂CH(CH₃)₂ I.1.588 CH(CH₃)—CO—OCH₃ CH₂CH(CH₃)₂ I.1.589 C(CH₃)₂—CO—OCH₃ CH₂CH(CH₃)₂ I.1.590 CH═CH—CO—OCH₃ CH₂CH(CH₃)₂ I.1.591 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH₂CH(CH₃)₂ I.1.592 CH₂CH₂OCH₃ CH₂CH(CH₃)₂ I.1.593 CH₂CH₂OC₂H₅ CH₂CH(CH₃)₂ I.1.594 CH₂CH₂SCH₃ CH₂CH(CH₃)₂ I.1.595 CH₂CH₂S(O)CH₃ CH₂CH(CH₃)₂ I.1.596 CH₂CH₂SO₂CH₃ CH₂CH(CH₃)₂ I.1.597 CH(CH₃)C₂H₅ CH(CH₃)CH₂CH₃ I.1.598 CH(CH₃)CH₂CH₂CH₃ CH(CH₃)CH₂CH₃ I.1.599 CH₂CH(CH₃)CH₂CH₃ CH(CH₃)CH₂CH₃ I.1.600 CH₂CH₂CH(CH₃)₂ CH(CH₃)CH₂CH₃ I.1.601 CH₂CHF₂ CH(CH₃)CH₂CH₃ I.1.602 CH₂CF₃ CH(CH₃)CH₂CH₃ I.1.603 CH₂CH—Cl CH(CH₃)CH₂CH₃ I.1.604 CH₂CH₂Br CH(CH₃)CH₂CH₃ I.1.605 CH₂CH₂CN CH(CH₃)CH₂CH₃ I.1.606 CH(CH₃)CN CH(CH₃)CH₂CH₃ I.1.607 CH₂CH(CH₃)CN CH(CH₃)CH₂CH₃ I.1.608 cyclopropyl CH(CH₃)CH₂CH₃ I.1.609 CH₂—cyclopropyl CH(CH₃)CH₂CH₃ I.1.610 cyclopentyl CH(CH₃)CH₂CH₃ I.1.611 CH₂-cyclopentyl CH(CH₃)CH₂CH₃ I.1.612 cyclohexyl CH(CH₃)CH₂CH₃ I.1.613 CH₂CH═CH₂ CH(CH₃)CH₂CH₃ I.1.614 C(CH₃)═CH₂ CH(CH₃)CH₂CH₃ I.1.615 CH═CHCH₃ CH(CH₃)CH₂CH₃ I.1.616 CH₂CH═CHCH₃ CH(CH₃)CH₂CH₃ I.1.617 CH₂CF═CF₂ CH(CH₃)CH₂CH₃ I.1.618 CH₂—C≡CH CH(CH₃)CH₂CH₃ I.1.619 CH(CH₃)—C≡CH CH(CH₃)CH₂CH₃ I.1.620 OH CH(CH₃)CH₂CH₃ I.1.621 OCH₃ CH(CH₃)CH₂CH₃ I.1.622 CH₂—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.623 CH₂—CH₂—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.624 CH₂—CO—OC₂H₅ CH(CH₃)CH₂CH₃ I.1.625 CH(CH₃)—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.626 C(CH₃)₂—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.627 CH═CH—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.628 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH(CH₃)CH₂CH₃ I.1.629 CH₂CH₂OCH₃ CH(CH₃)CH₂CH₃ I.1.630 CH₂CH₂OC₂H₅ CH(CH₃)CH₂CH₃ I.1.631 CH₂CH₂SCH₃ CH(CH₃)CH₂CH₃ I.1.632 CH₂CH₂S(O)CH₃ CH(CH₃)CH₂CH₃ I.1.633 CH₂CH₂SO₂CH₃ CH(CH₃)CH₂CH₃ I.1.634 CH(CH₃)C₂H₅ C(CH₃)₃ I.1.635 CH₂CH(CH₃)₂ C(CH₃)₃ I.1.636 C(CH₃)₃ C(CH₃)₃ I.1.637 CH(CH₃)CH₂CH₂CH₃ C(CH₃)₃ I.1.638 CH₂CH(CH₃)CH₂CH₃ C(CH₃)₃ I.1.639 CH₂CH₂CH(CH₃)₂ C(CH₃)₃ I.1.640 CH₂CHF₂ C(CH₃)₃ I.1.641 CH₂CF₃ C(CH₃)₃ I.1.642 CH₂CH₂Cl C(CH₃)₃ I.1.643 CH₂CH₂Br C(CH₃)₃ I.1.644 CH₂CH₂CN C(CH₃)₃ I.1.645 CH(CH₃)CN C(CH₃)₃ I.1.646 CH₂CH(CH₃)CN C(CH₃)₃ I.1.647 cyclopropyl C(CH₃)₃ I.1.648 CH₂-cyclopropyl C(CH₃)₃ I.1.649 cyclopentyl C(CH₃)₃ I.1.650 CH₂-cyclopentyl C(CH₃)₃ I.1.651 cyclohexyl C(CH₃)₃ I.1.652 CH₂CH═CH₂ C(CH₃)₃ I.1.653 C(CH₃)═CH₂ C(CH₃)₃ I.1.654 CH═CHCH₃ C(CH₃)₃ I.1.655 CH₂CH═CHCH₃ C(CH₃)₃ I.1.656 CH₂CF═CF₂ C(CH₃)₃ I.1.657 CH₂—C≡CH C(CH₃)₃ I.1.658 CH(CH₃)—C≡CH C(CH₃)₃ I.1.659 OH C(CH₃)₃ I.1.660 OCH₃ C(CH₃)₃ I.1.661 CH₂—CO—OCH₃ C(CH₃)₃ I.1.662 CH₂—CH₂—CO—OCH₃ C(CH₃)₃ I.1.663 CH₂—CO—OC₂H₅ C(CH₃)₃ I.1.664 CH(CH₃)—CO—OCH₃ C(CH₃)₃ I.1.665 C(CH₃)₂—CO—OCH₃ C(CH₃)₃ I.1.666 CH═CH—CO—OCH₃ C(CH₃)₃ I.1.667 C(CH₃)₂—CO—OCH₂—CHCH₂ C(CH₃)₃ I.1.668 CH₂CH₂OCH₃ C(CH₃)₃ I.1.669 CH₂CH₂OC₂H₅ C(CH₃)₃ I.1.670 CH₂CH₂SCH₃ C(CH₃)₃ I.1.671 CH₂CH₂S(O)CH₃ C(CH₃)₃ I.1.672 CH₂CH₂—SO₂—CH₃ C(CH₃)₃ I.1.673 —CH₂—CH₂—CH₂—CH₂— I.1.674 —CH₂—CH₂—CH₂—CH₂—CH₂— I.1.675 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— I.1.676 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— I.1.677 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— I.1.678 —CH₂—CH₂—CH₂—CH₂—CH(CH₂CH₂Cl)— I.1.679 —CH₂—CH₂—CH₂—CH(CH₂CH₂Cl)—CH₂— I.1.680 —CH₂—CH₂—CH(CH₂CH₂Cl)—CH₂—CH₂— I.1.681 —CH═CH—CH₂—CH₂— I.1.682 —CH₂—CH═CH—CH₂— I.1.683 —CH═CH—CH₂—CH₂—CH₂— I.1.684 CH₂—CH═CH═CH₂—CH₂— I.1.685 —CH₂—CH₂—O—CH₂—CH₂— I.1.686 —CH₂—CH₂—O—CH(CH₃)—CH₂— I.1.687 —CH₂—CH₂—O—CH₂—CH(CH₃)— I.1.688 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— I.1.689 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—

Extraordinary preference is also given to the compounds of the formula I.2, in particular to the compounds of the formulae I.2.1 to I.2.689 which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen.

Extraordinary preference is also given to the compounds of the formula I.3, in particular to the compounds of the formulae I.3.1 to I.3.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur.

Extraordinary preference is also given to the compounds of the formula I.4, in particular to the compounds of the formulae I.4.1 to I.4.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond.

Extraordinary preference is also given to the compounds of the formula I.5, in particular to the compounds of the formulae I.5.1 to I.5.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂.

Extraordinary preference is also given to the compounds of the formula I.6, in particular to the compounds of the formulae I.6.1 to I.6.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR².

Extraordinary preference is also given to the compounds of the formula I.7, in particular to the compounds of the formulae I.7.1 to I.7.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.8, in particular to the compounds of the formulae I.8.1 to I.8.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.9, in particular to the compounds of the formulae I.9.1 to I.9.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.10, in particular to the compounds of the formulae I.10.1 to I.10.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.11, in particular to the compounds of the formulae I.11.1 to I.11.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.12, in particular to the compounds of the formulae I.12.1 to I.12.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.13, in particular to the compounds of the formulae I.13.1 to I.13.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen.

Extraordinary preference is also given to the compounds of the formula I.14, in particular to the compounds of the formulae I.14.1 to I.14.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen and B is oxygen.

Extraordinary preference is also given to the compounds of the formula I.15, in particular to the compounds of the formulae I.15.1 to I.15.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen and B is sulfur.

Extraordinary preference is also given to the compounds of the formula I.16, in particular to the compounds of the formulae I.16.1 to I.16.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen and B is a bond.

Extraordinary preference is also given to the compounds of the formula I.17, in particular to the compounds of the formulae I.17.1 to I.17.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen and Y is SO₂.

Extraordinary preference is also given to the compounds of the formula I.18, in particular to the compounds of the formulae I.18.1 to I.18.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen and Y is SO₂NR².

Extraordinary preference is also given to the compounds of the formula I.19, in particular to the compounds of the formulae I.19.1 to I.19.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.20, in particular to the compounds of the formulae I.20.1 to I.20.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen, B is oxygen and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.21, in particular to the compounds of the formulae I.21.1 to I.21.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen, B is sulfur and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.22, in particular to the compounds of the formulae I.22.1 to I.22.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen, B is a bond and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.23, in particular to the compounds of the formulae I.23.1 to I.23.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen, Y is SO₂ and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.24, in particular to the compounds of the formulae I.24.1 to I.24.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is hydrogen, Y is SO₂NR² and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formula I.25, in particular to the compounds of the formulae I.25.1 to I.25.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.26, in particular to the compounds of the formulae I.26.1 to I.26.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.27, in particular to the compounds of the formulae I.27.1 to I.27.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.28, in particular to the compounds of the formulae I.28.1 to I.28.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.29, in particular to the compounds of the formulae I.29.1 to I.29.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.30, in particular to the compounds of the formulae I.30.1 to I.30.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.31, in particular to the compounds of the formulae I.31.1 to I.31.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.32, in particular to the compounds of the formulae I.32.1 to I.32.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is oxygen and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.33, in particular to the compounds of the formulae I.33.1 to I.33.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is sulfur and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.34, in particular to the compounds of the formulae I.34.1 to I.34.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is a bond and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.35, in particular to the compounds of the formulae I.35.1 to I.35.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.36, in particular to the compounds of the formulae I.36.1 to I.36.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formula I.37, in particular to the compounds of the formulae I.37.1 to I.37.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q²² (where A¹⁰ and A¹¹=oxygen, A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.38, in particular to the compounds of the formulae I.38.1 to I.38.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q²² (where A¹⁰ and A¹¹=oxygen, A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.39, in particular to the compounds of the formulae I.39.1 to I.39.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q²² (where A¹⁰ and A¹¹=oxygen, A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.40, in particular to the compounds of the formulae I.40.1 to I.40.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q²² (where A¹⁰ and A¹¹=oxygen, A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.41, in particular to the compounds of the formulae I.41.1 to I.41.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q²² (where A¹⁰ and A¹¹=oxygen, A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.42, in particular to the compounds of the formulae I.42.1 to I.42.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q²² (where A¹⁰ and A¹¹=oxygen, A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.43, in particular to the compounds of the formulae I.43.1 to I.43.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.44, in particular to the compounds of the formulae I.44.1 to I.44.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.45, in particular to the compounds of the formulae I.45.1 to I.45.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.46, in particular to the compounds of the formulae I.46.1 to I.46.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.47, in particular to the compounds of the formulae I.47.1 to I.47.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.48, in particular to the compounds of the formulae I.48.1 to I.48.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formula I.49, in particular to the compounds of the formulae I.49.1 to I.49.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q²⁷ (where A¹³=oxygen, R³⁴, R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.50, in particular to the compounds of the formulae I.50.1 to I.50.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q²⁷ (where A¹³=oxygen, R³⁴, R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.51, in particular to the compounds of the formulae I.51.1 to I.51.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q²⁷ (where A¹³=oxygen, R³⁴, R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.52, in particular to the compounds of the formulae I.52.1 to I.52.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q (where A¹³=oxygen, R³⁴, R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.53, in particular to the compounds of the formulae I.53.1 to I.53.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q²⁷ (where A¹³=oxygen, R³⁴, R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.54, in particular to the compounds of the formulae I.54.1 to I.54.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen, R³⁴, R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.55, in particular to the compounds of the formulae I.55.1 to I.55.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formula I.56, in particular to the compounds of the formulae I.56.1 to I.56.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formula I.57, in particular to the compounds of the formulae I.57.1 to I.57.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formula I.58, in particular to the compounds of the formulae I.58.1 to I.58.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formula I.59, in particular to the compounds of the formulae I.59.1 to I.59.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formula I.60, in particular to the compounds of the formulae I.60.1 to I.60.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formula I.61, in particular to the compounds of the formulae I.61.1 to I.61.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formula I.62, in particular to the compounds of the formulae I.62.1 to I.62.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formula I.63, in particular to the compounds of the formulae I.63.1 to I.63.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formula I.64, in particular to the compounds of the formulae I.64.1 to I.64.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formula I.65, in particular to the compounds of the formulae I.65.1 to I.65.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formula I.66, in particular to the compounds of the formulae I.66.1 to I.66.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formula I.67, in particular to the compounds of the formulae I.67.1 to I.67.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³² (where R³⁷=chlorine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.68, in particular to the compounds of the formulae I.68.1 to I.68.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=chlorine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.69, in particular to the compounds of the formulae I.69.1 to I.69.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=chlorine, R³⁸=difluoromethoxy, R³⁹ methyl).

Extraordinary preference is also given to the compounds of the formula I.70, in particular to the compounds of the formulae I.70.1 to I.70.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=chlorine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.71, in particular to the compounds of the formulae I.71.1 to I.71.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=chlorine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.72, in particular to the compounds of the formulae I.72.1 to I.72.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=chlorine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.73, in particular to the compounds of the formulae I.73.1 to I.73.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.74, in particular to the compounds of the formulae I.74.1 to I.74.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.75, in particular to the compounds of the formulae I.75.1 to I.75.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.76, in particular to the compounds of the formulae I.76.1 to I.76.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.77, in particular to the compounds of the formulae I.77.1 to I.77.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.78, in particular to the compounds of the formulae I.78.1 to I.78.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.79, in particular to the compounds of the formulae I.79.1 to I.79.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.80, in particular to the compounds of the formulae I.80.1 to I.80.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is oxygen and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.81, in particular to the compounds of the formulae I.81.1 to I.81.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is sulfur and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.82, in particular to the compounds of the formulae I.82.1 to I.82.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is a bond and Q is Q³² (where R³1=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.83, in particular to the compounds of the formulae I.83.1 to I.83.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.84, in particular to the compounds of the formulae I.84.1 to I.84.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.85, in particular to the compounds of the formulae I.85.1 to I.85.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³² (where R³⁷=chlorine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.86, in particular to the compounds of the formulae I.86.1 to I.86.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=chlorine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.87, in particular to the compounds of the formulae I.87.1 to I.87.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=chlorine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.88, in particular to the compounds of the formulae I.88.1 to I.88.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=chlorine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.89, in particular to the compounds of the formulae I.89.1 to I.89.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=chlorine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.90, in particular to the compounds of the formulae I.90.1 to I.90.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=chlorine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.91, in particular to the compounds of the formulae I.91.1 to I.91.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.92, in particular to the compounds of the formulae I.92.1 to I.92.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.93, in particular to the compounds of the formulae I.93.1 to I.93.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.94, in particular to the compounds of the formulae I.94.1 to I.94.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.95, in particular to the compounds of the formulae I.95.1 to I.95.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.96, in particular to the compounds of the formulae I.96.1 to I.96.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.97, in particular to the compounds of the formulae I.97.1 to I.97.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.98, in particular to the compounds of the formulae I.98.1 to I.98.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is oxygen and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.99, in particular to the compounds of the formulae I.99.1 to I.99.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is sulfur and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.100, in particular to the compounds of the formulae I.100.1 to I.100.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is a bond and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.101, in particular to the compounds of the formulae I.101.1 to I.101.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.102, in particular to the compounds of the formulae I.102.1 to I.102.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.103, in particular to the compounds of the formulae I.103.1 to I.103.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³² (where R³⁷=chlorine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.104, in particular to the compounds of the formulae I.104.1 to I.104.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=chlorine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.105, in particular to the compounds of the formulae I.105.1 to I.105.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=chlorine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.106, in particular to the compounds of the formulae I.106.1 to I.106.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=chlorine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.107, in particular to the compounds of the formulae I.107.1 to I.107.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=chlorine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.108, in particular to the compounds of the formulae I.108.1 to I.108.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=chlorine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.109, in particular to the compounds of the formulae I.109.1 to I.109.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.110, in particular to the compounds of the formulae I.110.1 to I.110.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.111, in particular to the compounds of the formulae I.111.1 to I.111.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.112, in particular to the compounds of the formulae I.112.1 to I.112.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.113, in particular to the compounds of the formulae I.113.1 to I.113.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.114, in particular to the compounds of the formulae I.114.1 to I.114.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I. 115, in particular to the compounds of the formulae I.115.1 to I.115.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.116, in particular to the compounds of the formulae I.116.1 to I.116.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is oxygen and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.117, in particular to the compounds of the formulae I.117.1 to I.117.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is sulfur and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.118, in particular to the compounds of the formulae I.118.1 to I.118.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, B is a bond and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.119, in particular to the compounds of the formulae I.119.1 to I.119.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.120, in particular to the compounds of the formulae I.120.1 to I.120.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q³² (where R³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula I.121, in particular to the compounds of the formulae I.121.1 to I.121.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.122, in particular to the compounds of the formulae I.122.1 to I.122.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.123, in particular to the compounds of the formulae I.123.1 to I.123.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.124, in particular to the compounds of the formulae I.124.1 to I.124.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.125, in particular to the compounds of the formulae I.125.1 to I.125.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.126, in particular to the compounds of the formulae I.126.1 to I.126.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.127, in particular to the compounds of the formulae I.127.1 to I.127.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q³⁹ (where A¹=oxygen, A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formula I.128, in particular to the compounds of the formulae I.128.1 to I.128.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q³⁹ (where A¹ oxygen, A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formula I.129, in particular to the compounds of the formulae I.129.1 to I.129.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q³⁹ (where A¹=oxygen, A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formula I.130, in particular to the compounds of the formulae I.130.1 to I.130.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q³⁹ (where A¹=oxygen, A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formula I.131, in particular to the compounds of the formulae I.131.1 to I.131.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q³⁹ (where A¹=oxygen, A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formula I.132, in particular to the compounds of the formulae I.132.1 to I.132.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³⁹ (where A¹=oxygen, A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formula I.133, in particular to the compounds of the formulae I.133.1 to I.133.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.134, in particular to the compounds of the formulae I.134.1 to I.134.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.135, in particular to the compounds of the formulae I.135.1 to I.135.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.136, in particular to the compounds of the formulae I.136.1 to I.136.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.137, in particular to the compounds of the formulae I.137.1 to I.137.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.138, in particular to the compounds of the formulae I.138.1 to I.138.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.139, in particular to the compounds of the formulae I. 139.1 to I.139.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶=sulfur, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —H₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.140, in particular to the compounds of the formulae I.140.1 to I.140.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶=sulfur, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.141, in particular to the compounds of the formulae I.141.1 to I.141.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶=sulfur, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.142, in particular to the compounds of the formulae I.142.1 to I.142.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶=sulfur, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.143, in particular to the compounds of the formulae I.143.1 to I.143.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶=sulfur, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.144, in particular to the compounds of the formulae I.144.1 to I.144.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶=sulfur, A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.145, in particular to the compounds of the formulae I.145.1 to I.145.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.146, in particular to the compounds of the formulae I.146.1 to I.146.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.147, in particular to the compounds of the formulae I.147.1 to I.147.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.148, in particular to the compounds of the formulae I.148.1 to I.148.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.149, in particular to the compounds of the formulae I.149.1 to I.149.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.150, in particular to the compounds of the formulae I.150.1 to I.150.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.151, in particular to the compounds of the formulae I.151.1 to I.151.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶=oxygen, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.152, in particular to the compounds of the formulae I.152.1 to I.152.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶=oxygen, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.153, in particular to the compounds of the formulae I.153.1 to I.153.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶=oxygen, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.154, in particular to the compounds of the formulae I.154.1 to I.154.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶=oxygen, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.155, in particular to the compounds of the formulae I.155.1 to I.155.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶=oxygen, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formula I.156, in particular to the compounds of the formulae I.156.1 to I.156.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶=oxygen, A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

The benzenesulfonamide derivatives of the formula I can be obtained by different routes, for example by one of the processes below:

Process A

Appropriately substituted aromatic compounds of the formula VIII are, by chlorosulfonylation, converted into the corresponding benzenesulfonyl chlorides of the formula VII which are then reacted with ammonia to give the corresponding sulfonamides of the formula V. The sulfonamides of the formula V are then reacted with (thio)phosgene of the formula VI to give the benzenesulfonyl iso(thio)cyanates of the formula II which are then reacted with amines of the formula III or alcohols or thiols of the formula IV to give the desired benzenesulfonamide derivatives of the formula I, where X³ is hydrogen, Y is —C(A)B and B is NR², oxygen or sulfur and the other radicals are as defined under claim 1:

Q in formula VIII denotes the radicals Q¹ to Q³⁹ mentioned above or a substituent which is a precursor suitable for the synthesis of Q¹ to Q³⁹, for example a nitro or carboxyl group.

The chlorosulfonylation of the aromatic compounds of the formula VIII to give the corresponding benzenesulfonyl chlorides of the formula VII is usually carried out at temperatures of from 0° C. to 150° C., preferably from 20° C. to 130° C., particularly preferably from 30° C. to 110° C., using, for example, chlorosulfonic acid, sulfonyl chloride (SO₂Cl₂) or using sulfonyl chloride in the presence of chlorosulfonic acid in an inert organic solvent [cf. Houben-Weyl, Methoden der organischen Chemie (Methods of organic chemistry), Vol. 9, 1955, pp. 572-579].

Suitable solvents are halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, nitriles, such as acetonitrile and propionitrile, and also chlorosulfonic acid, particularly preferably chlorosulfonic acid.

It is also possible to use mixtures of the solvents mentioned.

If appropriate, this reaction can also be carried out in the presence of a metal catalyst, for example aluminum chloride, analogously to a Friedel-Crafts reaction [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 578-579].

Suitable acids and acid catalysts include inorganic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids, such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride.

The acid catalysts are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess, or, if appropriate, as solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of chlorosulfonic acid or sulfonyl chloride, based on VIII, or to work directly in chlorosulfonic acid, as solvent.

The reaction mixtures are worked up in a customary manner, for example by mixing with water, phase separation and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of viscous oils which can be freed from volatile components or purified under reduced pressure and at moderately elevated temperatures. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

Furthermore, it is also possible to cleave dialkyl sulfides with chlorine in the presence of water, followed by conversion into the corresponding benzenesulfonyl chlorides of the formula VII [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 580-582].

Analogously, it is also possible to convert thiophenols into the corresponding benzenesulfonyl chlorides of the formula VII [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, p. 582].

Benzenesulfonyl chlorides of the formula VII can also be prepared by reacting benzenesulfonic acids with chlorinating agents such as thionyl chloride, phosgene, phosphorus trichloride or phosphorus pentachloride [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 564-568].

It is also possible to convert anilides via their diazonium salts with sulfur dioxide in the presence of copper(II) chloride (Meerwein reaction) into the corresponding benzenesulfonyl chlorides of the formula VII [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, p. 579-580].

The starting materials required for preparing the compounds I are known from the literature [for example CAS 112, 157842; JP 01/168662] or can be prepared in accordance with the literature cited.

Benzenesulfonyl chlorides of the formula VII in which Q is Q⁷ are known, for example, from WO 02/38562.

The preparation of benzenesulfonyl chlorides of the formula VII in which Q is Q²¹ is described, for example, in U.S. Pat. No. 5,169,430.

Benzenesulfonyl chlorides of the formula VII in which Q is Q³² are known, for example, from WO 96/15115.

The preparation of benzenesulfonyl chlorides of the formula VII in which Q is Q³⁸ is described, for example, in WO 95/02580.

Benzenesulfonyl chlorides of the formula VII having other radicals Q can be prepared analogously to the methods mentioned above (cf. for example JP 05/164386). Further precursors are described in Böger, Wakabayashi, Peroxidizing Herbicides, Springer Verlag 1999.

The subsequent reaction of the benzenesulfonyl chlorides of the formula VII with gaseous or aqueous ammonia to give the corresponding sulfonamides of the formula V where

X³=hydrogen is usually carried out at temperatures of from −10° C. to 50° C., preferably from 0° C. to 30° C., particularly preferably from 5° C. to 15° C., in an inert organic solvent, if appropriate in the presence of a base [cf. U.S. Pat. No. 5,169,430; WO 95102580; Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 398-400 and 605].

Ammonia is preferably used in an excess of from 200 to 230%; however, it is also possible to use an auxiliary base.

Suitable auxiliary bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide, and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, 1,2-dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butylmethyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethylformamide and dimethylacetamide, particularly preferably dioxane, tetrahydrofuran, 1,2-dichloroethane, toluene or cyclohexane.

It is also possible to use mixtures of the solvents mentioned.

Work-up and isolation of the products can be carried out in a manner known per se.

Further sulfonamides of formula V can be prepared by analogous reaction of benzenesulfonyl chlorides of the formula VII with an amine H₂NX³.

Sulfonamides of the formula V, in which Q is Q⁷ are described, for example, in WO 02/38562.

U.S. Pat. No. 5,169,430 and WO 95/02580 describe sulfonamides of the formula V in which Q is Q²¹ and Q²⁸, respectively.

The reaction of the sulfonamides of the formula V where X³=hydrogen with (thio)phosgene of the formula VI to give benzenesulfonyl iso(thio)cyanates of the formula II is usually carried out at temperatures of from 50° C. to 110° C., preferably from 60° C. to 90° C., in an inert organic solvent, if appropriate in the presence of a catalyst [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 11, 2, 1985, p. 1106; U.S. Pat. No. 4,379,769; DD 238 522].

Suitable catalysts are, for example, aliphatic isocyanates, such as, for example, n-propyl isocyanate, isopropyl isocyanate or n-butyl isocyanate.

The catalyst is generally employed in a substoichiometric amount of from 5% to 15% per mole of sulfonamide of the formula V.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, particularly preferably toluene, 1,2-dichloroethane or chlorobenzene.

It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of VI, based on V.

Work-up and isolation of the products can be carried out in a manner known per se.

The conversion of the sulfonamides of the formula V where X³=hydrogen into benzenesulfonyl iso(thio)cyanates of the formula II can also be carried out using diphosgene [ClC(O)OCCl₃] or using carbon disulfide in phosgene.

Expediently, the sulfonamides of the formula V where X³=hydrogen can also be initially pre-treated with thionyl chloride under reflux and then be reacted with phosgene to give benzenesulfonyl iso(thio)cyanates of the formula II (cf. DE 43 22 726).

Benzenesulfonyl iso(thio)cyanates of the formula II can also be prepared by reacting sulfonamides of the formula V where X³=hydrogen with chlorosulfonyl isocyanate (cf. DE 31 32 944).

Benzenesulfonyl iso(thio)cyanates of the II can furthermore be prepared in a manner known per se by reacting benzenesulfonyl chlorides of the formula VII with alkali metal isocyanates (cf. U.S. Pat. No. 4,546,179).

The reaction of benzenesulfonyl iso(thio)cyanates of the II with a primary amine of the formula III or an alcohol or thiol of the formula IV to give the desired benzenesulfonamide derivatives of the formula I where X³=hydrogen, Y=—C(A)B and B=NR², oxygen or sulfur is usually carried out at temperatures of from 0° C. to 120° C., preferably from 10° C. to 100° C., particularly preferably from 20° C. to 70° C., in an inert organic solvent [cf. EP 162 723].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably from 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C₅-C₈-alkanes; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene; halogenated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran and also nitriles, such as acetonitrile and propionitrile, particularly preferably tetrahydrofuran, dioxane and 1,2-dichloroethane.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, it is possible to add, before or during the reaction, a base, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine or 1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The benzenesulfonyl iso(thio)cyanates of the II are generally reacted in equimolar amounts with the primary amine of the formula III or the alcohol or thiol of the formula IV. It may be advantageous to employ an excess of III or IV, based on II.

Work-up and isolation of the products can be carried out in a manner known per se.

Process B

Sulfonamides of the formula V are reacted with (thio)carbamates of the formula IX to give the desired benzenesulfonamide derivatives of the formula I, where Y is —C(A)B and B is NR² and the other radicals are as defined under claim 1:

Z in formula IX denotes a C₁-C₆-alkyl or phenyl radical, where both radicals for their part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-alkoxycarbonyl.

This reaction is usually carried out at temperatures of from 0° C. to 120° C., preferably from 20° C. to 100° C., in an inert organic solvent [cf. EP 141 777 and EP 101 670].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably 1,2-dichloroethane, tetrahydrofuran, tert-butyl methyl ether and toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine and 1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolar amounts with the (thio)carbamate of the formula IX. It may be advantageous to employ an excess of IX, based on V.

The work-up and isolation of the products can be carried out in a manner known per se.

By analogous reaction with carboxylic acid derivatives ZO(A)R¹, it is possible to prepare benzenesulfonamide derivatives of the formula I where Y=—C(A)B and B=a bond.

Process C

Sulfonamides of the formula V can be reacted with iso(thio)cyanates of the formula X to give the desired benzenesulfonamide derivatives of the formula I where Y is —C(A)B and B is NH and the other radicals are as defined under claim 1:

This reaction is usually carried out at temperatures of from 0° C. to 150° C., preferably from 10° C. to 100° C., in an inert organic solvent [cf. EP 234 352].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably 1,2-dichloroethane, tetrahydrofuran, ethyl acetate, tert-butyl methyl ether, acetone and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine or 2,4,6-collidine.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolar amounts with an iso(thio)cyanate of the formula X. It may be advantageous to employ an excess of X, based on V.

To bring the reaction to completion, the reaction mixture may, after addition of the components, be stirred at from 0 to 120° C., preferably from 10 to 100° C., in particular from 20 to 80° C., for another 20 min. to 24 h.

Work-up and isolation of the products can be carried out in a manner known per se.

Process D

Sulfonamides of the formula V can be reacted with halides of the formula XI to give the desired benzenesulfonamide derivatives of the formula I:

Hal in formula XI denotes halogen, such as fluorine, chlorine, bromine, particularly preferably chlorine.

This reaction is usually carried out at temperatures of from 0° C. to 150° C., preferably from 10° C. to 100° C., in an inert organic solvent [cf. JP 05/194386, CAS 120, 134277].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably 1,2-dichloroethane, tetrahydrofuran, ethyl acetate, acetonitrile and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine or 2,4,6-collidine.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolar amounts with the isocyanate or isothiocyanate of the formula X. It may be advantageous to employ an excess of XI, based on V.

To bring the reaction to completion, the reaction mixture may, after addition of the components, be stirred at from 0 to 120° C., preferably from 10 to 100° C., in particular from 20 to 80° C., for another 20 min to 24 h.

Work-up and isolation of the products can be carried out in a manner known per se.

Analogously to process D described above, it is also possible to react sulfonamides of the formula V with anhydrides of the formula XII A[C(=A)-R¹]₂  XII to give the desired benzenesulfonamide derivatives of the formula I in which Y is —C(A)B where B is a bond and the other radicals are as defined under claim 1. Process E

Sulfonyl(thio)carbamates of the formula XIII are reacted with amines of the formula XIV to give the desired benzenesulfonamide derivatives of the formula I where Y is —C(A)B and B is NR² and the other radicals are as defined under claim 1:

Z in formula XIII is C₁-C₆-alkyl or phenyl, where both radicals may for their part be partially or fully halogenated and/or may carry one to three radicals from the group consisting of nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-alkoxycarbonyl.

This reaction is usually carried out at temperatures of from 0° C. to 120° C., preferably from 10° C. to 100° C., in an inert organic solvent [cf. EP 120 814; EP 101 407].

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably tetrahydrofuran, dioxane, dimethylformamide and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine and 1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonylcarbamates of the formula XII are generally reacted in equimolar amounts with an amine of the formula XIV. It may be advantageous to employ an excess of XIV, based on XII.

Work-up and isolation of the products can be carried out in a manner known per se.

The starting materials required for preparing the compounds I are known from the literature [cf. for example, CAS 112, 157842; JP 01/168662], or they can be prepared in accordance with the literature cited.

Process F

Compounds of the formula I in which the radicals Q carry the substituents R³, R⁴, R⁷, R¹¹, R¹⁸, R¹⁹, R²⁴, R²⁷, R²⁹, R³², R³⁹, R⁴⁴-R⁴⁷ on their nitrogen atoms [these radicals denoting, inter alia, C₁-C₆-alkyl or amino, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino] can be prepared by reacting, either prior to the synthesis of the sulfonamide side chain (i.e. at the stage of the aromatic compounds of the formula VIII) or after synthesis of the sulfonamide side chain, with an alkyl halide, alkyl sulfate, alkyl tosylate or an electrophilic aminating agent of the formula XVII, analogously to the methods described in the literature.

Examples of electrophilic aminating agents of the formula XVII are 2,4-dinitrophenylhydroxylamine and o-mesitylenesulfonyl hydroxylamine.

The benzenesulfonyl chlorides of the formula VII mentioned above can be converted, for example, by action of alcohols, expediently in the presence of a base, into the corresponding benzenesulfonyl esters [Houben-Weyl, Methoden der organischen Synthese, Vol. 9, 1955, p. 663]. The benzenesulfonyl esters can then be alkylated or aminated on the free nitrogen atoms of the corresponding radicals Q. Subsequently, the benzenesulfonyl esters can be hydrolyzed again [cf. Kocienski, Protecting groups, Thieme-Verlag 1994; Greene, Wuts, Protecting groups in organic synthesis, Wiley 1999; Houben-Weyl, Methoden der organischen Chemie, Vol. E5 part 1, 1985, p. 223f.).

By way of example, an amination at the radical Q=Q²¹ is shown here. The aminations of the other radicals Q and alkylations at the radicals Q can be carried out analogously. This route affords, for example, sulfonic acids of the formula XVI. These can then be converted using methods known from the literature into the desired benzenesulfonamide derivatives of the formula I.

This reaction is usually carried out at temperatures of from 10° C. to 80° C., preferably from 20° C. to 40° C., in an inert organic solvent in the presence of a base [cf. DE 19 652 431; WO 01/83459].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethyl formamide and dimethylacetamide, particularly preferably tetrahydrofuran, dioxane, acetonitrile and also dimethylformamide.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, for example alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to potassium carbonate and also calcium carbonate.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent.

The starting materials are generally reacted with one another in equimolar amounts. However, it may also be advantageous to employ an excess of XVII, based on XV.

Work-up and isolation of the products can be carried out in a manner known per se.

The starting materials required for preparing the compounds I are known from the literature [for example CAS 112, 157842; JP 01168662], or they can be prepared in accordance with the literature cited.

The present invention also provides benzenesulfonyl iso(thio)cyanates of the formula II

where X¹, X², A and Q are as defined under claim 1.

The particularly preferred embodiments of the intermediates with respect to the variables correspond to those of the radicals X¹, X², A and Q of formula I.

Particular preference is given to intermediates of the formula IV in which

-   -   X¹ is hydrogen, fluorine or chlorine;         -   particularly preferably hydrogen or fluorine;         -   especially preferably fluorine;     -   X² is hydrogen, cyano, CS—NH₂ or halogen;         -   particularly preferably hydrogen, halogen such as fluorine             and chlorine;         -   especially preferably chlorine; and     -   Q is Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷, Q²⁰, Q²¹, Q²², Q²³,         Q²⁴, Q²⁷, Q³¹, Q³², Q³⁴, Q³⁸ or Q³⁹,         -   particularly preferably Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³,             Q¹⁷, Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹,         -   especially preferably Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or             Q³⁹,         -   with extraordinary preference Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or             Q³⁹,         -   with most extraordinary preference Q²¹, Q³² or Q³⁸.

PREPARATION EXAMPLES Example 1 2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonamide

With stirring, 1.6 g (93.8 mmol) of ammonia gas were, at 0° C., introduced into a mixture of 18 g (44.6 mmol) of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonylchloride in tetrahydrofuran (THF). Then, at 10° C., ethyl acetate was added and the mixture was acidified with 1N hydrochloric acid. The phases were separated and the aqueous phase was extracted, and the combined organic phases were then washed, dried and the solvent was removed. Customary purification methods gave 14.4 g (82.4% of theory) of the title compound (m.p.: 257-258° C.).

Example 2 2-Chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate

At 60° C., 7.4 g (62.3 mmol) of thionyl chloride were added dropwise with stirring to a suspension of 10.0 g (24.9 mmol) of 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonylamide in 1,2-dichloroethane. The mixture was then boiled under reflux for 4 h. The mixture was then cooled to 60° C., a catalytic amount of pyridine was added and phosgene was introduced under reflux for 12 h until a clear solution was obtained. After cooling to 30° C., the product was freed from the solvent. This gave 11.6 g (98% of theory) of the title compound.

¹H-NMR (400 MHz, CDCl₃) δ [ppm]=8.12 (d, 1H), 7.55 (d, 1H), 6.38 (s, 1H), 3.57 (s, 3H).

Example 3 2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonyl isocyanate

10.0 g (26.1 mmol) of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonamide were reacted analogously to the method described in Example 2. This gave 13.4 g (99% of theory) of the title compound.

¹H-NMR (400 MHz, CDCl₃) δ [ppm]=8.02 (s, 1H), 7.76 (d, 2H), 7.5 (d, 1H), 6.38 (s, 1H), 3.70 (s, 3H).

Example 4 (No. 3.32) Benzyl{2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]phenyl}sulfonylcarbamate

With stirring, 0.6 g (1.4 mmol) of 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate in 1,2-dichloroethane was added to a solution of 0.15 g (1.4 mmol) of benzyl alcohol in methylene chloride, and the reaction mixture was stirred overnight. Removal of the solvent and customary purification methods gave 0.4 g (52% of theory) of the title compound as a colorless solid (m.p.: 231-232° C.).

Example 5 (No. 2.26) 3-[4-Chloro-2-fluoro-5-{[isopropyl(methyl)amino]carbonylaminosulfonyl}phenyl]-1-methyl-2,4-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

With stirring, 1.0 g (2.34 mmol) of 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonyl isocyanate in 1,2-dichloroethane was added to a solution of 0.34 g (4.68 mmol) of N-methylisopropylamine in 1,2-dichloroethane, and the mixture was stirred overnight. The reaction mixture was concentrated, the residue was taken up in methylene chloride and 0.5N hydrochloric acid was added. The organic phase was then dried and the solvent was removed. This gave 0.5 g (42% of theory) of the title compound as a colorless solid (m.p.: 145° C.).

Example 6 (No. 4.5) N-isobutynyl-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1-(2H)-pyrimidinyl)]benzenesulfonamide

With stirring, 0.15 g (1.43 mmol) of isobutyryl chloride was added to a mixture of 0.5 g (1.3 mmol) of 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonyl isocyanate, 0.26 g (2.61 mmol) of triethylamine and catalytic amounts of N,N-dimethylaminopyridine in methylene chloride, and the mixture was stirred overnight. The reaction mixture was washed with 1N hydrochloric acid and dried and the solvent was removed. This gives 0.6 g (96% of theory) of the title compound as a colorless solid (m.p.: 114-116° C.).

In addition to the compounds above, Tables 2 to 4 list further benzenesulfonamide derivatives of the formula I which were prepared or are preparable in a manner similar to the processes described above.

TABLE 2 2

No. X¹ X² R¹ R² R²⁹ m.p. [° C.] 2.1 H Cl CH₃ H CH₃ 2.2 H Cl CH₃ H NH₂ 2.3 H Cl CH₃ CH₃ CH₃ 2.4 H Cl CH₃ CH₃ NH₂ 2.5 H Cl OCH₃ CH₃ CH₃  95 2.6 H Cl C₂H₅ H CH₃ 2.7 H Cl C₂H₅ H NH₂ 2.8 H Cl C₂H₅ C₂H₅ CH₃ 2.9 H Cl CH₂CH₂CH₃ H CH₃ 2.10 H Cl CH₂CH₂CH₃ H NH₂ 2.11 H Cl CH(CH₃)₂ H CH₃ 2.12 H Cl CH(CH₃)₂ CH₃ CH₃ 197 2.13 H Cl CH₂═CH—CH₂ H CH₃ 2.14 H Cl 4-methoxy-6-methyl- H CH₃ 209-211 pyrimidin-2-yl 2.15 H Cl 4,6-dimethoxy- H CH₃ 208-212 pyrimidin-2-yl 2.16 H Cl 4-methoxy-6-methyl- H CH₃ 146-175 1,3,5-triazin-2- yl 2.17 F Cl CH₃ H CH₃ 228-230 2.18 F Cl CH₃ H NH₂ 2.19 F Cl CH₃ CH₃ CH₃ 198-205 2.20 F Cl CH₃ CH₃ NH₂ 2.21 F Cl C₂H₅ H CH₃ 2.22 F Cl C₂H₅ H NH₂ 2.23 F Cl C₂H₅ CH₃ CH₃ 2.24 F Cl CH₂CH₂CH₃ H CH₃ 2.25 F Cl CH₂CH₂CH₃ CH₃ CH₃ 2.26 F Cl CH(CH₃)₂ CH₃ CH₃ 145 (decomposition) 2.27 F Cl CH(CH₃)₂ CH(CH₃)₂ CH₃ 179-181 2.28 F Cl CH(CH₃)C≡CH CH₃ CH₃ 160-165 2.29 F Cl C₆H₅ H CH₃ 160 2.30 F Cl —(CH₂)₅— CH₃ 2.31 F Cl —(CH₂)₆— CH₃ 2.32 Cl Cl CH₃ H CH₃ 234-235 2.33 Cl Cl CH₃ CH₃ CH₃ 2.34 Cl Cl CH₃ CH₃ NH₂ 2.35 Cl Cl C₂H₅ H CH₃ 2.36 Cl Cl CH₂CH₂CH₃ H CH₃ 2.37 F Cl CH(CH₃)₂ H NH₂

TABLE 3 3

No. X¹ X² A B R¹ R²⁹ m.p. [° C.] 3.1 H Cl O O CH₃ CH₃ 120-148 3.2 H Cl O O C₂H₅ CH₃ 189-190 3.3 H Cl O O CH₂CH₂CH₃ CH₃ 3.4 H Cl O O CH(CH₃)₂ CH₃ 3.5 H Cl O O (CH₂)₃CH₃ CH₃ 194-195 3.6 H Cl O O CH(CH₃)CH₂CH₃ CH₃ 3.7 H Cl O O CH₂CH(CH₃)₂ CH₃ 3.8 H Cl O O C(CH₃)₃ CH₃ 3.9 H Cl O O (CH₂)₄CH₃ CH₃ 3.10 H Cl O O cyclopentyl CH₃ 114-116 3.11 H Cl O O CH₂CH₂Cl CH₃ 3.12 H Cl O O (CH₂)OCH₃ CH₃ 3.13 H Cl O O (CH₂)SCH₃ CH₃ 3.14 H Cl O O CH₂CH₂CN CH₃ 3.15 H Cl O S CH₃ CH₃ 3.16 H Cl O S C₂H₅ CH₃ 3.17 H Cl O S CH₂CH₂CH₃ CH₃ 3.18 F Cl O O CH₃ CH₃ 120-135 3.19 F Cl O O C₂H₅ CH₃ 228-231 3.20 F Cl O O CH₂CH₂CH₃ CH₃ 203 3.21 F Cl O O CH(CH₃)₂ CH₃ 228-230 3.22 F Cl O O (CH₂)₃CH₃ CH₃ 238 3.23 F Cl O O CH(CH₃)CH₂CH₃ CH₃ 195-198 3.24 F Cl O O CH₂CH(CH₃)₂ CH₃ 233-235 3.25 F Cl O O C(CH₃)₃ CH₃ 185 3.26 F Cl O O (CH₂)₄CH₃ CH₃ 235 3.27 F Cl O O cyclopentyl CH₃ 214 3.28 F Cl O O CH₂CH₂Cl CH₃ 3.29 F Cl O O (CH₂)OCH₃ CH₃ 3.30 F Cl O O (CH₂)SCH₃ CH₃ 3.31 F Cl O O CH₂CH₂CN CH₃ 3.32 F Cl O O CH₂C₆H₅ CH₃ 231-232 3.33 F Cl O S CH₃ CH₃ 3.34 F Cl O S C₂H₅ CH₃ 3.35 F Cl O S CH₂CH₂CH₃ CH₃ 3.36 Cl Cl O S CH₃ CH₃ 3.37 Cl Cl O S C₂H₅ CH₃ 3.38 Cl Cl O S CH₂CH₂CH₃ CH₃ 3.39 Cl Cl O O CH₃ CH₃ 218-220 3.40 Cl Cl O O C₂H₅ CH₃ 235-237 3.41 F Cl O O CH₂COOCH₃ CH₃ 142-160 3.42 F Cl O O C(CH₃)₂CH₂OCH₃ CH₃ 178

TABLE 4 4

No. X¹ X² R¹ R²⁹ m.p. [° C.] 4.1 H Cl H CH₃ 4.2 H Cl CH₃ CH₃ 4.3 H Cl C₂H₅ CH₃ 4.4 H Cl CH₂CH₂CH₃ CH₃ 4.5 H Cl CH(CH₃)₂ CH₃ 114-116 4.6 H Cl (CH₂)₃CH₃ CH₃ 4.7 H Cl CH(CH₃)CH₂CH₃ CH₃ 4.8 H Cl CH₂CH(CH₃)₂ CH₃ 4.9 H Cl cyclopentyl CH₃ 4.10 H Cl CH₃ NH₂ 4.11 H Cl C₂H₅ NH₂ 4.12 H Cl CH₂CH₂CH₃ NH₂ 4.13 F Cl CH₃ CH₃ 269 (decomposition) 4.14 F Cl C₂H₅ CH₃ 229-230 4.15 F Cl CH₂CH₂CH₃ CH₃ 4.16 F Cl CH(CH₃)₂ CH₃ 243-245 4.17 F Cl CH₂Cl CH₃ 4.18 F Cl CF₃ CH₃ 4.19 F Cl C₆H₅ CH₃ 4.20 F Cl 2-Cl—C₆H₄ CH₃ 4.21 F Cl 3-Cl—C₆H₄ CH₃ 4.22 F Cl 4-Cl—C₆H₄ CH₃ 4.23 F Cl CH₂(4-CH₃—C₆H₄) CH₃ 4.24 Cl Cl CH₃ CH₃ 275-277 4.25 Cl Cl C₂H₅ CH₃ 225-230 4.26 Cl Cl CH₂CH₂CH₃ CH₃ 4.27 Cl Cl CH₂CH(CH₃)₂ CH₃ 4.28 Cl Cl CH₃ NH₂ 4.29 Cl Cl C₂H₅ NH₂ 4.30 Cl Cl CH₂CH₂CH₃ NH₂ Biological Activity

The benzenesulfonamide derivatives of the formula I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds of the formula I, or the herbicidal compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, lpomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

Furthermore, the benzenesulfonamide derivatives of the formula I and their agriculturally useful salts are also suitable for the desiccation and/or defoliation of plants.

As desiccants, they are particularly suitable for desiccating the above-ground parts of crop plants such as potatoes; oilseed rape, sunflowers and soybeans. This allows completely mechanical harvesting of these important crop plants.

Also of economic interest is

-   -   the concentrated, within a certain time, fruit drop or the         reduction of the adherence of the fruits to the plant, for         example in the case of citrus fruit, olives or other species and         varieties of pomaceous fruit, stone fruit and hard-shelled         fruit, thus facilitating the harvesting of these fruits, and         also     -   the controlled defoliation of useful plants, in particular         cotton.

The drop, promoted by using compounds of the formula I according to the invention and agriculturally useful salts thereof, is a result of the formation of abscission tissue between fruits or leaves and the shoot of the plants.

The defoliation of cotton is of very particular economic interest, since it facilitates harvesting. At the same time, the reduced period of time within which the individual plants mature results in a better quality of the harvested fiber material.

The compounds of the formula I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should ensure a very fine distribution of the active compounds according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for formulating crop protection agents.

Essentially, suitable inert auxiliaries include:

mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substrates, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The formulation examples below illustrate the production of such preparations:

-   -   I 20 parts by weight of an active compound of the formula I are         dissolved in a mixture composed of 80 parts by weight of         alkylated benzene, 10 parts by weight of the adduct of 8 to 10         mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide,         5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts         by weight of the adduct of 40 mol of ethylene oxide to 1 mol of         castor oil. Pouring the solution into 100,000 parts by weight of         water and finely distributing it therein gives an aqueous         dispersion which comprises 0.02% by weight of the active         compound of the formula I.     -   II 20 parts by weight of an active compound of the formula I are         dissolved in a mixture composed of 40 parts by weight of         cyclohexanone, 30 parts by weight of isobutanol, 20 parts by         weight of the adduct of 7 mol of ethylene oxide to 1 mol of         isooctylphenol and 10 parts by weight of the adduct of 40 mol of         ethylene oxide to 1 mol of castor oil. Pouring the solution into         100,000 parts by weight of water and finely distributing it         therein gives an aqueous dispersion which comprises 0.02% by         weight of the active compound of the formula I.     -   III 20 parts by weight of an active compound of the formula I         are dissolved in a mixture composed of 25 parts by weight of         cyclohexanone, 65 parts by weight of a mineral oil fraction of         boiling point 210 to 280° C. and 10 parts by weight of the         adduct of 40 mol of ethylene oxide to 1 mol of castor oil.         Pouring the solution into 100,000 parts by weight of water and         finely distributing it therein gives an aqueous dispersion which         comprises 0.02% by weight of the active compound of the formula         I.     -   IV 20 parts by weight of an active compound of the formula I are         mixed thoroughly with 3 parts by weight of sodium         diisobutylnaphthalene sulfonate, 17 parts by weight of the         sodium salt of a lignosulfonic acid from a sulfite waste liquor         and 60 parts by weight of pulverulent silica gel, and the         mixture is ground in a hammer mill. Finely distributing the         mixture in 20,000 parts by weight of water gives a spray mixture         which comprises 0.1% by weight of the active compound of the         formula I.     -   V 3 parts by weight of an active compound of the formula I are         mixed with 97 parts by weight of finely divided kaolin. This         gives a dust which comprises 3% by weight of the active compound         of the formula I.     -   VI 20 parts by weight of an active compound of the formula I are         mixed intimately with 2 parts by weight of calcium         dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol         polyglycol ether, 2 parts by weight of the sodium salt of a         phenol/urea/formaldehyde condensate and 68 parts by weight of a         paraffinic mineral oil. This gives a stable oily dispersion.     -   VII 1 part by weight of an active compound of the formula I is         dissolved in a mixture composed of 70 parts by weight of         cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol         and 10 parts by weight of ethoxylated castor oil. This gives a         stable emulsion concentrate.     -   VIII 1 part by weight of an active compound of the formula I is         dissolved in a mixture composed of 80 parts by weight of         cyclohexanone and 20 parts by weight of Wettol^(R) EM 31         (=nonionic emulsifier based on ethoxylated castor oil). This         gives a stable emulsion concentrate.

The herbicidal compositions or the compounds of the formula I can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of the compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

To widen the activity spectrum and to achieve synergistic effects, the benzenesulfonamide derivatives of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-hetaroyl/aroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenyl-propionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formula I, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

USE EXAMPLES Herbicidal Efficacy

The herbicidal activity of the benzenesulfonamide derivatives of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, emulsified or suspended in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant form, and only then treated with the active compounds, emulsified or suspended in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

The application rate for the pre- and post-emergence treatment was from 62.5 to 3.1 g of a.s./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were composed of the following species:

Scientific Name Common Name Abutilon theophrasti Velvet leaf Amaranthus retroflexus Pigweed Chenopodium album Common lambsquarters Commelina benghalensis Bengal commelina Galium aparine Cleavers harrif Ipomoea hederacea Morning glory Pharbitis purpurea Common morning glory Polygonum convolvulus Wild buckwheat Polygonum persicaria Ladysthumb Solanum nigrum Common nightshade

At application rates of 12.5 and 6.2 g/ha, the compounds 3.1 and 3.18 (Table 3) showed very good pre-emergence activity against the unwanted plants pigweed, common lambsquarters, common morning glory and wild buckwheat.

Furthermore, compounds 3.24 (Table 3) and 4.16 (Table 4), when applied by the pre-emergence method at application rates of 6.2 and 3.1 g/ha, effected very good control of the unwanted plants velvet leaf, pigweed, common lambsquarters and morning glory.

The effectiveness of compound 3.32 (Table 3), when applied by the pre-emergence method at application rates of 62.5 and 31.2 g/ha, was very good against the unwanted plants velvet leaf, pigweed, common lambsquarters and common nightshade.

At application rates of 15.6 and 7.8 g/ha, the compounds 3.27, 3.19, 3.20 and 3.22 (Table 3) showed very good post-emergence activity against the unwanted plants pigweed, common lambsquarters, common morning glory and ladysthumb.

Furthermore, compounds 2.29 (Table 2) and 3.26 (Table 3), when applied by the post-emergence method at application rates of 15.6 and 7.8 g/ha, effected very good control of the unwanted plants pigweed, common lambsquarters and common morning glory.

The effectiveness of compound 3.42 (Table 3), when applied by the post-emergence method at application rates of 15.63 g/ha, was very good against the unwanted plants velvet leaf, common morning glory and ladiesthumb.

At application rates of 15.63 g/ha, the compounds 3.41 (Table 3) and 4.14 (Table 4) showed very good post-emergence activity against the unwanted plants pigweed, cleavers harrif and ladiesthumb.

Furthermore, compound 2.17 (Table 2), when applied by the post-emergence method at application rates of 15.63 g/ha, effected very good control of the unwanted plants velvet leaf, common lambsquarters and Bengal commelina.

The effectiveness of compound 2.28 (Table 2), when applied by the post-emergence method at application rates of 15.63 g/ha, was very good against the unwanted plants pigweed, common lambsquarters and common morning glory.

At application rates of 15.63 g/ha, the compound 2.27 (Table 2) showed very good post-emergence activity against the unwanted plants pigweed and common morning glory.

USE EXAMPLES Desiccant/Defoliant Efficacy

The test plants used were young 4-leaf cotton plants (without cotyledons) which were grown under greenhouse conditions (rel. atmospheric humidity 50 to 70%; day/night temperature 27/20° C.).

The leaves of the young cotton plants were sprayed to runoff point with aqueous preparations of the active compounds (with addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac® LF 700¹⁾, based on the spray liquor). The amount of water applied was 1000 l/ha (converted). After 13 days, the number of leaves that had been shed and the degree of defoliation in % were determined. ¹⁾ A low-foam nonionic surfactant from BASF AG

The untreated control plants did not lose any leaves. 

1. A compound which is a benzenesulfonamide derivative of the formula I

in which the variables are as defined below: X¹ is halogen; X² is chlorine; X³ is hydrogen; Y is a group —C(A)B; A is oxygen; B is oxygen or sulfur; R¹ is hydrogen, C₁-C₈-alkyl, C₃-C₇-cycloalkyl, or phenyl-C₁-C₄ alkyl, wherein C₁-C₈ alkyl may be substituted by C₁-C₈alkoxy or C₁-C₈ alkoxycarbonyl; Q is

A⁸ and A⁹ are oxygen; R²⁹ is hydrogen, C₁-C₆ alkyl, or amino; R³⁰ is C₁-C₆ haloalkyl; R³¹ is hydrogen; or an agriculturally useful salt thereof.
 2. A compound of claim 1, in which X¹ is fluorine or chlorine.
 3. A process for preparing a compound of claim 1, where X³ is hydrogen, which comprises reacting a benzenesulfonyl iso(thio)cyanate of the formula II

where X¹, X², A and Q are as defined in claim 1, with an alcohol or thiol of the formula IV HBR¹ III where B=NR² IV where B=O, S where R¹ is as defined in claim
 1. 4. An herbicidal composition comprising a herbicidally effective amount of at least one benzenesulfonamide derivative of the formula I or an agriculturally useful salt of I according to claim 1 and further comprising auxiliaries customary for formulating crop protection agents.
 5. An herbicidal composition for the desiccation and/or defoliation of plants, comprising such an amount of at least one benzenesulfonamide derivative of the formula I or an agriculturally useful salt of I according to claim 1 that acts as a desiccant and/or defoliant, and further comprising auxiliaries customary for formulating crop protection agents.
 6. A process for preparing herbicidally effective compositions, which comprises mixing a herbicidally effective amount of at least one benzenesulfonamide derivative of the formula I or an agriculturally useful salt of I according to claim 1 and auxiliaries customary for formulating crop protection agents.
 7. A process for preparing compositions having desiccant and/or defoliant action, which comprises mixing a desiccant and/or defoliant effective amount of at least one compound according to claim 1 and auxiliaries customary for formulating crop protection agents.
 8. A method for controlling unwanted vegetation, wherein a herbicidally effective amount of at least one benzenesulfonamide derivative of the formula I or an agriculturally useful salt of I according to claim 1 is allowed to act on the unwanted vegetation, their habitat and/or on their seeds.
 9. A method for the desiccation and/or defoliation of plants, which comprises allowing a desiccant and/or defoliant effective amount of at least one compound according to claim 1 to act on the plants. 